| Year |
Citation |
Score |
| 2020 |
Lu J, Bart AG, Wu Q, Criscione KR, McLeish MJ, Scott EE, Grunewald GL. Structure-Based Drug Design of Bisubstrate Inhibitors of Phenylethanolamine -Methyltransferase Possessing Low Nanomolar Affinity at Both Substrate Binding Domains. Journal of Medicinal Chemistry. PMID 33147410 DOI: 10.1021/acs.jmedchem.0c01475 |
0.324 |
|
| 2010 |
Drinkwater N, Vu H, Lovell KM, Criscione KR, Collins BM, Prisinzano TE, Poulsen SA, McLeish MJ, Grunewald GL, Martin JL. Fragment-based screening by X-ray crystallography, MS and isothermal titration calorimetry to identify PNMT (phenylethanolamine N-methyltransferase) inhibitors. The Biochemical Journal. 431: 51-61. PMID 20642456 DOI: 10.1042/Bj20100651 |
0.381 |
|
| 2010 |
GRUNEWALD GL, PARADKAR VM. ChemInform Abstract: A Regioselective Synthesis of 8,9-Dichloro-2,3,4,5-tetrahydro-1H-2- benzazepine (LY134046), a Potent Phenylethanolamine N- Methyltransferase Inhibitor. Cheminform. 23: no-no. DOI: 10.1002/chin.199239227 |
0.309 |
|
| 2009 |
Drinkwater N, Gee CL, Puri M, Criscione KR, McLeish MJ, Grunewald GL, Martin JL. Molecular recognition of physiological substrate noradrenaline by the adrenaline-synthesizing enzyme PNMT and factors influencing its methyltransferase activity. The Biochemical Journal. 422: 463-71. PMID 19570037 DOI: 10.1042/Bj20090702 |
0.348 |
|
| 2009 |
Wu Q, Caine JM, Thomson SA, Slavica M, Grunewald GL, McLeish MJ. Time-dependent inactivation of human phenylethanolamine N-methyltransferase by 7-isothiocyanatotetrahydroisoquinoline. Bioorganic & Medicinal Chemistry Letters. 19: 1071-4. PMID 19171483 DOI: 10.1016/J.Bmcl.2009.01.014 |
0.377 |
|
| 2008 |
Grunewald GL, Seim MR, Bhat SR, Wilson ME, Criscione KR. Synthesis of 4,5,6,7-tetrahydrothieno[3,2-c]pyridines and comparison with their isosteric 1,2,3,4-tetrahydroisoquinolines as inhibitors of phenylethanolamine N-methyltransferase. Bioorganic & Medicinal Chemistry. 16: 542-59. PMID 18024134 DOI: 10.1016/J.Bmc.2007.08.066 |
0.821 |
|
| 2007 |
Gee CL, Drinkwater N, Tyndall JD, Grunewald GL, Wu Q, McLeish MJ, Martin JL. Enzyme adaptation to inhibitor binding: a cryptic binding site in phenylethanolamine N-methyltransferase. Journal of Medicinal Chemistry. 50: 4845-53. PMID 17845018 DOI: 10.1021/Jm0703385 |
0.382 |
|
| 2007 |
Grunewald GL, Seim MR, Regier RC, Criscione KR. Exploring the active site of phenylethanolamine N-methyltransferase with 1,2,3,4-tetrahydrobenz[h]isoquinoline inhibitors. Bioorganic & Medicinal Chemistry. 15: 1298-310. PMID 17126018 DOI: 10.1016/J.Bmc.2006.11.010 |
0.792 |
|
| 2006 |
Grunewald GL, Seim MR, Regier RC, Martin JL, Gee CL, Drinkwater N, Criscione KR. Comparison of the binding of 3-fluoromethyl-7-sulfonyl-1,2,3,4-tetrahydroisoquinolines with their isosteric sulfonamides to the active site of phenylethanolamine N-methyltransferase. Journal of Medicinal Chemistry. 49: 5424-33. PMID 16942016 DOI: 10.1021/Jm060466D |
0.822 |
|
| 2006 |
Grunewald GL, Seim MR, Lu J, Makboul M, Criscione KR. Application of the Goldilocks effect to the design of potent and selective inhibitors of phenylethanolamine N-methyltransferase: balancing pKa and steric effects in the optimization of 3-methyl-1,2,3,4-tetrahydroisoquinoline inhibitors by beta-fluorination. Journal of Medicinal Chemistry. 49: 2939-52. PMID 16686536 DOI: 10.1021/Jm051262K |
0.822 |
|
| 2005 |
Gee CL, Tyndall JD, Grunewald GL, Wu Q, McLeish MJ, Martin JL. Mode of binding of methyl acceptor substrates to the adrenaline-synthesizing enzyme phenylethanolamine N-methyltransferase: implications for catalysis. Biochemistry. 44: 16875-85. PMID 16363801 DOI: 10.1021/Bi051636B |
0.336 |
|
| 2005 |
Wu Q, Gee CL, Lin F, Tyndall JD, Martin JL, Grunewald GL, McLeish MJ. Structural, mutagenic, and kinetic analysis of the binding of substrates and inhibitors of human phenylethanolamine N-methyltransferase. Journal of Medicinal Chemistry. 48: 7243-52. PMID 16279783 DOI: 10.1021/Jm050568O |
0.377 |
|
| 2005 |
Grunewald GL, Lu J, Criscione KR, Okoro CO. Inhibitors of phenylethanolamine N-methyltransferase devoid of alpha2-adrenoceptor affinity. Bioorganic & Medicinal Chemistry Letters. 15: 5319-23. PMID 16169723 DOI: 10.1016/J.Bmcl.2005.08.033 |
0.559 |
|
| 2005 |
Grunewald GL, Romero FA, Criscione KR. Nanomolar inhibitors of CNS epinephrine biosynthesis: (R)-(+)-3-fluoromethyl-7-(N-substituted aminosulfonyl)-1,2,3,4-tetrahydroisoquinolines as potent and highly selective inhibitors of phenylethanolamine N-methyltransferase1. Journal of Medicinal Chemistry. 48: 1806-12. PMID 15771426 DOI: 10.1021/Jm049594X |
0.591 |
|
| 2005 |
Grunewald GL, Romero FA, Seim MR, Criscione KR, Deupree JD, Spackman CC, Bylund DB. Exploring the active site of phenylethanolamine N-methyltransferase with 3-hydroxyethyl- and 3-hydroxypropyl-7-substituted-1,2,3,4-tetrahydroisoquinolines. Bioorganic & Medicinal Chemistry Letters. 15: 1143-7. PMID 15686930 DOI: 10.1016/J.Bmcl.2004.12.013 |
0.82 |
|
| 2005 |
Grunewald GL, Romero FA, Chieu AD, Fincham KJ, Bhat SR, Criscione KR. Exploring the active site of phenylethanolamine N-methyltransferase: 3-alkyl-7-substituted-1,2,3,4-tetrahydroisoquinoline inhibitors. Bioorganic & Medicinal Chemistry. 13: 1261-73. PMID 15670935 DOI: 10.1016/J.Bmc.2004.11.015 |
0.706 |
|
| 2005 |
Grunewald GL, Romero FA, Criscione KR. 3-hydroxymethyl-7-(N-substituted aminosulfonyl)-1,2,3,4-tetrahydroisoquinoline inhibitors of phenylethanolamine N-methyltransferase that display remarkable potency and selectivity. Journal of Medicinal Chemistry. 48: 134-40. PMID 15634007 DOI: 10.1021/Jm049368N |
0.654 |
|
| 2004 |
Romero FA, Vodonick SM, Criscione KR, McLeish MJ, Grunewald GL. Inhibitors of phenylethanolamine N-methyltransferase that are predicted to penetrate the blood-brain barrier: design, synthesis, and evaluation of 3-fluoromethyl-7-(N-substituted aminosulfonyl)-1,2,3,4-tetrahydroisoquinolines that possess low affinity toward the alpha2-adrenoceptor. Journal of Medicinal Chemistry. 47: 4483-93. PMID 15317460 DOI: 10.1021/Jm0400653 |
0.698 |
|
| 2004 |
Wu Q, Criscione KR, Grunewald GL, McLeish MJ. Phenylethanolamine N-methyltransferase inhibition: re-evaluation of kinetic data. Bioorganic & Medicinal Chemistry Letters. 14: 4217-20. PMID 15261273 DOI: 10.1016/J.Bmcl.2004.06.009 |
0.42 |
|
| 2004 |
McMillan FM, Archbold J, McLeish MJ, Caine JM, Criscione KR, Grunewald GL, Martin JL. Molecular recognition of sub-micromolar inhibitors by the epinephrine-synthesizing enzyme phenylethanolamine N-methyltransferase. Journal of Medicinal Chemistry. 47: 37-44. PMID 14695818 DOI: 10.1021/Jm0205752 |
0.432 |
|
| 2003 |
Stone EA, Grunewald GL, Lin Y, Ahsan R, Rosengarten H, Kramer HK, Quartermain D. Role of epinephrine stimulation of CNS alpha1-adrenoceptors in motor activity in mice. Synapse (New York, N.Y.). 49: 67-76. PMID 12710017 DOI: 10.1002/Syn.10212 |
0.4 |
|
| 2002 |
Lankin DC, Grunewald GL, Romero FA, Oren IY, Snyder JP. The NH---FC dipole orientation effect for pendant exocyclic CH(2)F. Organic Letters. 4: 3557-60. PMID 12375886 DOI: 10.1021/ol026358c |
0.425 |
|
| 2001 |
Martin JL, Begun J, McLeish MJ, Caine JM, Grunewald GL. Getting the adrenaline going: crystal structure of the adrenaline-synthesizing enzyme PNMT. Structure (London, England : 1993). 9: 977-85. PMID 11591352 DOI: 10.1016/S0969-2126(01)00662-1 |
0.367 |
|
| 2001 |
Grunewald GL, Dahanukar VH, Criscione KR. Effects of a 3-alkyl-, 4-hydroxy- and/or 8-aromatic-substituent on the phenylethanolamine N-methyltransferase inhibitor potency and alpha2-adrenoceptor affinity of 2,3,4,5-tetrahydro-1H-2-benzazepines. Bioorganic & Medicinal Chemistry. 9: 1957-65. PMID 11504632 DOI: 10.1016/S0968-0896(01)00112-2 |
0.757 |
|
| 2001 |
Grunewald GL, Caldwell TM, Li Q, Criscione KR. Synthesis and evaluation of 4-fluoro-8-substituted-2,3,4,5-tetrahydro-1H-2-benzazapines as selective inhibitors of phenylethanolamine N-methyltransferase versus the alpha(2)-adrenoceptor. Journal of Medicinal Chemistry. 44: 2849-56. PMID 11495596 DOI: 10.1021/Jm010147G |
0.787 |
|
| 2001 |
Grunewald GL, McLeish MJ, Criscione KR. Phenylethanolamine N-methyltransferase kinetics: bovine versus recombinant human enzyme. Bioorganic & Medicinal Chemistry Letters. 11: 1579-82. PMID 11412985 DOI: 10.1016/S0960-894X(01)00245-1 |
0.332 |
|
| 1999 |
Grunewald GL, Caldwell TM, Li Q, Dahanukar VH, McNeil B, Criscione KR. Enantiospecific synthesis of 3-fluoromethyl-, 3-hydroxymethyl-, and 3-chloromethyl-1,2,3,4-tetrahydroisoquinolines as selective inhibitors of phenylethanolamine N-methyltransferase versus the alpha(2)-adrenoceptor. Journal of Medicinal Chemistry. 42: 4351-61. PMID 10543879 DOI: 10.1021/Jm990086A |
0.828 |
|
| 1999 |
Grunewald GL, Caldwell TM, Li Q, Slavica M, Criscione KR, Borchardt RT, Wang W. Synthesis and biochemical evaluation of 3-fluoromethyl-1,2,3, 4-tetrahydroisoquinolines as selective inhibitors of phenylethanolamine N-methyltransferase versus the alpha(2)-adrenoceptor. Journal of Medicinal Chemistry. 42: 3588-601. PMID 10479290 DOI: 10.1021/Jm990045E |
0.781 |
|
| 1999 |
Grunewald GL, Caldwell TM, Li Q, Criscione KR. Synthesis and evaluation of 3-trifluoromethyl-7-substituted-1,2,3, 4-tetrahydroisoquinolines as selective inhibitors of phenylethanolamine N-methyltransferase versus the alpha(2)-adrenoceptor. Journal of Medicinal Chemistry. 42: 3315-23. PMID 10464018 DOI: 10.1021/Jm980734A |
0.785 |
|
| 1999 |
Grunewald GL, Caldwell TM, Li Q, Criscione KR. 1,3-Dimethyl-7-substituted-1,2,3,4-tetrahydroisoquinolines as probes for the binding orientation of tetrahydroisoquinoline at the active site of phenylethanolamine N-methyltransferase. Bioorganic & Medicinal Chemistry. 7: 869-80. PMID 10400340 DOI: 10.1016/S0968-0896(99)00031-0 |
0.783 |
|
| 1999 |
Grunewald GL, Dahanukar VH, Teoh B, Criscione KR. 3,7-Disubstituted-1,2,3,4-tetrahydroisoquinolines display remarkable potency and selectivity as inhibitors of phenylethanolamine N-methyltransferase versus the alpha2-adrenoceptor. Journal of Medicinal Chemistry. 42: 1982-90. PMID 10354406 DOI: 10.1021/Jm9807252 |
0.785 |
|
| 1999 |
Grunewald GL, Caldwell TM, Dahanukar VH, Jalluri RK, Criscione KR. Comparative molecular field analysis (CoMFA) models of phenylethanolamine N-methyltransferase (PNMT) and the alpha2-adrenoceptor: the development of new, highly selective inhibitors of PNMT. Bioorganic & Medicinal Chemistry Letters. 9: 481-6. PMID 10091706 DOI: 10.1016/S0960-894X(99)00022-0 |
0.794 |
|
| 1999 |
Grunewald GL, Dahanukar VH, Jalluri RK, Criscione KR. Synthesis, biochemical evaluation, and classical and three-dimensional quantitative structure-activity relationship studies of 7-substituted-1,2,3,4-tetrahydroisoquinolines and their relative affinities toward phenylethanolamine N-methyltransferase and the alpha2-adrenoceptor. Journal of Medicinal Chemistry. 42: 118-34. PMID 9888838 DOI: 10.1021/Jm980429P |
0.82 |
|
| 1997 |
Grunewald GL, Dahanukar VH, Caldwell TM, Criscione KR. Examination of the role of the acidic hydrogen in imparting selectivity of 7-(aminosulfonyl)-1,2,3,4-tetrahydroisoquinoline (SK&F 29661) toward inhibition of phenylethanolamine N-methyltransferase vs the alpha 2-adrenoceptor. Journal of Medicinal Chemistry. 40: 3997-4005. PMID 9406590 DOI: 10.1021/Jm960235E |
0.832 |
|
| 1996 |
Caine JM, Macreadie IG, Grunewald GL, McLeish MJ. Recombinant human phenylethanolamine N-methyltransferase: overproduction in Escherichia coli, purification, and characterization. Protein Expression and Purification. 8: 160-6. PMID 8812853 DOI: 10.1006/Prep.1996.0088 |
0.307 |
|
| 1996 |
Grunewald GL, Dahanukar VH, Ching P, Criscione KR. Effect of ring size or an additional heteroatom on the potency and selectivity of bicyclic benzylamine-type inhibitors of phenylethanolamine N-methyltransferase. Journal of Medicinal Chemistry. 39: 3539-46. PMID 8784452 DOI: 10.1021/Jm9508292 |
0.795 |
|
| 1996 |
Victory SF, Vander Velde DG, Jalluri RK, Grunewald GL, Georg GI. Relative stereochemistry and solution conformation of the novel paclitaxel-like antimitotic agent epothilone A Bioorganic and Medicinal Chemistry Letters. 6: 893-898. DOI: 10.1016/0960-894X(96)00139-4 |
0.73 |
|
| 1996 |
Cho WJ, Grunewald GL. Design and stereoselective synthesis of conformationally constrained analogues of zimeldine Archives of Pharmacal Research. 19: 168-170. DOI: 10.1007/Bf02976855 |
0.306 |
|
| 1994 |
Czaplinski KHA, Grunewald GL. A comparative molecular field analysis derived model of the binding of taxol® analogues to microtubules Bioorganic and Medicinal Chemistry Letters. 4: 2211-2216. DOI: 10.1016/S0960-894X(00)80073-6 |
0.348 |
|
| 1994 |
Grunewald GL, Dahanukar VH. Synthesis of 3-alkyl-8-substituted- and 4-hydroxy-8-substituted-2,3,4,5-tetrahydro-1H-2-benzazepines Journal of Heterocyclic Chemistry. 31: 1609-1617. DOI: 10.1002/Jhet.5570310656 |
0.68 |
|
| 1991 |
Grunewald GL, Palanki MS, Takusagawa F. Structures of two conformationally defined phenylethanolamines: exo-1,4-epoxy-2-formamido-1,2,3,4-tetrahydro-8-trifluoromethylnaphthale ne and exo-1,4-epoxy-2-formamido-1,2,3,4-tetrahydro-6-trifluoromethylnaphthale ne. Acta Crystallographica. Section C, Crystal Structure Communications. 47: 771-5. PMID 1863422 DOI: 10.1107/S0108270190007284 |
0.32 |
|
| 1991 |
Grunewald GL, Paradkar VM. A regioselective synthesis of 8,9-dichloro-2,3,4,5-tetrahydro-1H-2-benzazepine (LY134046), a potent phenylethanolamine N-methyltransferase inhibitor Bioorganic and Medicinal Chemistry Letters. 1: 59-60. DOI: 10.1016/S0960-894X(01)81091-X |
0.438 |
|
| 1991 |
Grunewald GL, Paradkar VM, Stillions DM, Ching F. A new procedure for regioselective synthesis of 8,9-dichloro-2,3,4,5-tetrahydro-1H2-benzazepine (LY134046) and its 3-methyl analogue as inhibitors of phenylethanolamine N-methyltransferase (PNMT) [1a] Journal of Heterocyclic Chemistry. 28: 1587-1592. DOI: 10.1002/Jhet.5570280622 |
0.388 |
|
| 1990 |
Grunewald GL, Kolar AJ, Palanki MSS, Paradkar VM, Reitz TJ, Sall DJ. One-step synthesis of trifluoromethyl- and of methoxy-substituted benzyne precursors Organic Preparations and Procedures International. 22: 747-753. DOI: 10.1080/00304949009457903 |
0.332 |
|
| 1989 |
Grunewald GL, Ye Q, Sall DJ, Criscione KR, Wise B. Conformational and steric aspects of phenylethanolamine and phenylethylamine analogues as substrates or inhibitors of phenylethanolamine N-methyltransferase. Molecular Pharmacology. 35: 93-7. PMID 2913486 |
0.344 |
|
| 1989 |
Ye QH, Grunewald GL. Conformationally restricted and conformationally defined tyramine analogues as inhibitors of phenylethanolamine N-methyltransferase. Journal of Medicinal Chemistry. 32: 478-86. PMID 2913308 DOI: 10.1021/Jm00122A032 |
0.466 |
|
| 1989 |
Brouillette WJ, Grunewald GL, Brown GB, DeLorey TM, Akhtar MS, Liang G. Sodium channel binding and anticonvulsant activities for the enantiomers of a bicyclic 2,4-oxazolidinedione and monocyclic models. Journal of Medicinal Chemistry. 32: 1577-80. PMID 2544727 DOI: 10.1021/Jm00127A029 |
0.622 |
|
| 1988 |
Grunewald GL, Sall DJ, Monn JA. Synthesis and evaluation of 3-substituted analogues of 1,2,3,4-tetrahydroisoquinoline as inhibitors of phenylethanolamine N-methyltransferase. Journal of Medicinal Chemistry. 31: 824-30. PMID 3351861 DOI: 10.1021/Jm00399A024 |
0.47 |
|
| 1988 |
Grunewald GL, Sall DJ, Monn JA. Conformational and steric aspects of the inhibition of phenylethanolamine N-methyltransferase by benzylamines. Journal of Medicinal Chemistry. 31: 433-44. PMID 3339613 DOI: 10.1021/Jm00397A029 |
0.49 |
|
| 1988 |
Grunewald GL, Carter AE, Sall DJ, Monn JA. Conformational preference for the binding of biaryl substrates and inhibitors to the active site of phenylethanolamine N-methyltransferase. Journal of Medicinal Chemistry. 31: 60-5. PMID 3336033 DOI: 10.1021/Jm00396A010 |
0.518 |
|
| 1988 |
Grunewald GL, Ye Q, Kieffer L, Monn JA. Conformational requirements of substrates for activity with phenylethanolamine N-methyltransferase. Journal of Medicinal Chemistry. 31: 169-71. PMID 3336016 DOI: 10.1021/Jm00396A026 |
0.404 |
|
| 1988 |
Grunewald GL, Ye QH. Stereochemical aspects of phenylethanolamine analogues as substrates of phenylethanolamine N-methyltransferase. Journal of Medicinal Chemistry. 31: 1984-6. PMID 3172133 DOI: 10.1021/Jm00118A021 |
0.369 |
|
| 1988 |
Brouillette WJ, Brown GB, DeLorey TM, Shirali SS, Grunewald GL. Anticonvulsant activities of phenyl-substituted bicyclic 2,4-oxazolidinediones and monocyclic models. Comparison with binding to the neuronal voltage-dependent sodium channel. Journal of Medicinal Chemistry. 31: 2218-21. PMID 2846842 DOI: 10.1021/Jm00119A025 |
0.647 |
|
| 1988 |
Grunewald GL, Ye Q. Synthesis of benzobicyclo[3.2.1]octanes involving inversion of configuration via an N to O acetyl migration Journal of Organic Chemistry. 53: 4021-4026. DOI: 10.1021/Jo00252A026 |
0.327 |
|
| 1988 |
Grunewald GL, Creese MW, Weintraub HJR. Conformational preferences in alkylbenzenes and aryl-alkylamines: A comparative study using CAMSEQ, MM2 and molecular dynamics methods Journal of Computational Chemistry. 9: 315-326. DOI: 10.1002/Jcc.540090406 |
0.355 |
|
| 1987 |
Sall DJ, Grunewald GL. Inhibition of phenylethanolamine N-methyltransferase (PNMT) by aromatic hydroxy-substituted 1,2,3,4,-tetrahydroisoquinolines: further studies on the hydrophilic pocket of the aromatic ring binding region of the active site. Journal of Medicinal Chemistry. 30: 2208-16. PMID 3681890 DOI: 10.1021/Jm00395A006 |
0.445 |
|
| 1987 |
Grunewald GL, Markovich KM, Sall DJ. Binding orientation of amphetamine and norfenfluramine analogues in the benzonorbornene and benzobicyclo[3.2.1]octane ring systems at the active site of phenylethanolamine N-methyltransferase (PNMT) Journal of Medicinal Chemistry. 30: 2191-208. PMID 3681889 DOI: 10.1021/Jm00395A005 |
0.425 |
|
| 1986 |
Grunewald GL, Arrington HS, Bartlett WJ, Reitz TJ, Sall DJ. Binding requirements of phenolic phenylethylamines in the benzonorbornene skeleton at the active site of phenylethanolamine N-methyltransferase. Journal of Medicinal Chemistry. 29: 1972-82. PMID 3761316 |
0.308 |
|
| 1984 |
Brouillette WJ, Grunewald GL. Synthesis and anticonvulsant activity of some substituted lactams and amides. Journal of Medicinal Chemistry. 27: 202-6. PMID 6694169 DOI: 10.1002/Chin.198431234 |
0.69 |
|
| 1984 |
Liang NY, Chandra A, Tessel RE, Grunewald GL, Borchardt RT. Inhibitors of phenylethanolamine-N-methyltransferase: effects on brain catecholamine content and blood pressure in DOCA-salt hypertensive rats. Research Communications in Chemical Pathology and Pharmacology. 46: 319-29. PMID 6515125 DOI: 10.1016/S0022-5347(17)49412-2 |
0.301 |
|
| 1983 |
Reitz TJ, Grunewald GL. Carbon-13 nuclear magnetic resonance examination of benzonorbornene derivatives. Assignment of site of aromatic ring substitution in benzonorbornen-2-ones Organic Magnetic Resonance. 21: 596-601. DOI: 10.1002/Omr.1270211003 |
0.318 |
|
| 1982 |
Rafferty MF, Krass P, Borchardt RT, Grunewald GL. Importance of the aromatic ring in adrenergic amines. 8. 2-(Aminomethyl)-trans-2-decalols as inhibitors of norepinephrine N-methyltransferase. Journal of Medicinal Chemistry. 25: 1250-2. PMID 7143367 DOI: 10.1002/Chin.198311323 |
0.486 |
|
| 1982 |
Grunewald GL, Monn JA, Rafferty MF, Borchardt RT, Krass P. Probes of the active site of norepinephrine N-methyltransferase: effect of hydrophobic and hydrophilic interactions on side-chain binding of amphetamine and alpha-methylbenzylamine. Journal of Medicinal Chemistry. 25: 1248-50. PMID 7143366 DOI: 10.1002/Chin.198311322 |
0.535 |
|
| 1982 |
Rafferty MF, Borchardt RT, Grunewald GL. Directional probes of the hydrophobic component of the aromatic ring binding site of norepinephrine N-methyltransferase. Journal of Medicinal Chemistry. 25: 1204-8. PMID 7143357 DOI: 10.1002/Chin.198310180 |
0.461 |
|
| 1982 |
Rafferty MF, Wilson DS, Monn JA, Krass P, Borchardt RT, Grunewald GL. Importance of the aromatic ring in adrenergic amines. 7. Comparison of the stereoselectivity of norepinephrine N-methyltransferase for aromatic vs. nonaromatic substrates and inhibitors. Journal of Medicinal Chemistry. 25: 1198-204. PMID 7143356 DOI: 10.1002/Chin.198310168 |
0.542 |
|
| 1982 |
Grunewald GL, Pleiss MA, Rafferty MF. Conformational preferences of dopamine analogues for inhibition of norepinephrine N-methyltransferase. Conformationally defined adrenergic agents. Life Sciences. 31: 993-1000. PMID 7132559 DOI: 10.1016/0024-3205(82)90171-0 |
0.392 |
|
| 1981 |
Vincek WC, Aldrich CS, Borchardt RT, Grunewald GL. Importance of the aromatic ring in adrenergic amines. 5. Nonaromatic analogues of phenylethanolamine as inhibitors of phenylethanolamine N-methyltransferase: role of hydrophobic and steric interactions. Journal of Medicinal Chemistry. 24: 7-12. PMID 7205880 |
0.321 |
|
| 1981 |
Davis DP, Borchardt RT, Grunewald GL. Importance of the aromatic ring in adrenergic amines. 6. Nonaromatic analogues of phenylethanolamine as inhibitors of phenylethanolamine N-methyltransferase: role of pi-electronic and steric interactions. Journal of Medicinal Chemistry. 24: 12-6. PMID 7205869 DOI: 10.1002/Chin.198123180 |
0.423 |
|
| 1980 |
Grunewald GL, Reitz TJ, Hallett A, Rutledge CO, Vollmer S, Archuleta JM, Ruth JA. Pronounced pharmacological differences arising from minor structural changes in conformationally defined amphetamine analogues. Comparative evaluation of endo- and exo-2-amino- and endo- and exo-2-(methylamino)benzobicyclo[2.2.1]heptene and -benzobicylco[2.2.2]octene analogues. Conformationally defined adrenergic agents. 4. Journal of Medicinal Chemistry. 23: 614-20. PMID 7392028 DOI: 10.1021/Jm00180A006 |
0.314 |
|
| 1980 |
Grunewald GL, Kuttab SH, Pleiss MA, Mangold JB, Soine P. Conformationally defined aromatic amino acids. Synthesis and stereochemistry of 2-endo- and 2-exo-amino-1,2,3,4-tetrahydro-1,4-ethanonaphthalene-2-carboxylic acids (2-endo- and 2-exo-aminobenzobicycle[2.2.2]octene-2-carboxylic acids). Journal of Medicinal Chemistry. 23: 754-8. PMID 6772787 DOI: 10.1002/Chin.198050184 |
0.326 |
|
| 1980 |
Grunewald GL, Brouillette WJ, Finney JA. Synthesis of α-hydroxyamides via the cyanosilylation of aromatic ketones Tetrahedron Letters. 21: 1219-1220. DOI: 10.1016/S0040-4039(00)71375-X |
0.595 |
|
| 1979 |
Grunewald GL, Reitz TJ, Ruth JA, Vollmer S, Eiden LE, Rutledge CO. Inhibition of neuronal uptake of 3H-biogenic amines into rat cerebral cortex by partially and fully saturated derivatives of imipramine and desipramine. The importance of the aromatic ring in adrenergic amines--part 3. Biochemical Pharmacology. 28: 417-21. PMID 426859 DOI: 10.1016/0006-2952(79)90108-4 |
0.357 |
|
| 1979 |
Brouillette WJ, Smissman EE, Grunewald GL. N-acylcarbamates as intermediates in synthetic approaches to a bicyclic trimethylene-bridged 2,4-oxazolidinedione and hydantoin Journal of Organic Chemistry. 44: 839-843. DOI: 10.1021/Jo01319A039 |
0.715 |
|
| 1979 |
Grunewald GL, Creese MW, Walters DE. APPLICATION OF CNDO/2 CALCULATIONS AND X-RAY CRYSTALLOGRAPHIC ANALYSIS OF THE DESIGN OF CONFORMATIONALLY DEFINED ANALOGS OF METHAMPHETAMINE Acs Symposium Series. 439-487. |
0.407 |
|
| 1978 |
Grunewald GL, Walters DE, Kroboth TR. Synthesis of bridgehead hydroxyl-substituted benzobicyclo[3.2.1]octenes and -octadienes via an acyloin rearrangement in the benzobicyclo[2.2.2]octene ring system Journal of Organic Chemistry. 43: 3478-3481. DOI: 10.1021/Jo00412A012 |
0.562 |
|
| 1978 |
Grunewald GL, Davis DP. A new convenient synthesis of bridgehead substituted norbornenes Journal of Organic Chemistry. 43: 3074-3076. DOI: 10.1021/Jo00409A037 |
0.321 |
|
| 1978 |
Grunewald GL, Brouillette WJ. An ethoxycarbonyl migration from an amide nitrogen to oxygen Journal of Organic Chemistry. 43: 1839-1841. DOI: 10.1021/Jo00403A058 |
0.577 |
|
| 1977 |
Warner VD, Musto JD, Sane JN, Kim KH, Grunewald GL. Quantitative structure-activity relationships for 5-substituted 8-hydroxyquinolines as inhibitors of dental plaque. Journal of Medicinal Chemistry. 20: 92-6. PMID 401891 DOI: 10.1002/Chin.197721227 |
0.339 |
|
| 1976 |
Grunewald GL, Ruth JA, Kroboth TR, Kamdar BV, Patil PN, Salman KN. Conformationally defined adrenergic agents I: potentiation of levarterenol in rat vas deferens by endo- and exo- 2- aminobenzobicyclo[2.2.2]octenes, conformationally defined analogs of amphetamine. Journal of Pharmaceutical Sciences. 65: 920-3. PMID 932982 DOI: 10.1002/Jps.2600650632 |
0.371 |
|
| 1976 |
Grunewald GL, Grindel JM, Patil PN, Salman KN. Importance of the aromatic ring in adrenergic amines. 2. Synthesis and adrenergic activity of some nonaromatic six- and eight-membered ring analogs of beta-phenylethanolamine. Journal of Medicinal Chemistry. 19: 10-6. PMID 1534 DOI: 10.1002/Chin.197617174 |
0.413 |
|
| 1974 |
Zimmerman H, Grunewald G, Paufler R, Sherwin M. Additions and Corrections - Synthesis and Physical Properties of Barrelene, a Unique Möbius-like Molecule Journal of the American Chemical Society. 96: 4067-4067. DOI: 10.1021/Ja00819A602 |
0.462 |
|
| 1972 |
Grunewald GL, Warner AM, Hays SJ, Bussell RH, Seals MK. Medicinal chemistry of (10) annulenes and related compounds. 1. 11-Azatricyclo(4.4.1.0 1,6 )undecane, 11-azatricyclo(4.4.1.0 1,6 )undeca-3,8-diene, and 11-azabicyclo(4.4.1)undeca-1,3,5,7,9-pentaene as antiviral agents. Journal of Medicinal Chemistry. 15: 747-50. PMID 5043873 DOI: 10.1021/Jm00277A012 |
0.333 |
|
| 1972 |
Grunewald GL, Warner AM. Medicinal chemistry of (10)annulenes and related compounds. 2. N-(2-Chloroethyl) derivatives of 11-azatricyclo(4.4.1.0 1,6 )undecane, 11-azatricyclo(4.4.1.0 1,6 )undeca-3,8-diene, and 11-azabicyclo(4.4.1)undeca-1,3,5,7,9-pentaene. Journal of Medicinal Chemistry. 15: 1192-4. PMID 4654675 DOI: 10.1021/Jm00281A031 |
0.412 |
|
| 1969 |
Martin AR, Parulkar AP, Gusseck DJ, Anderson LJ, Grunewald GL, White AI. Substituted tetralins. I. Synthesis and analgesic activities of some 2-aminotetralins. Journal of Pharmaceutical Sciences. 58: 340-7. PMID 5782029 DOI: 10.1002/Jps.2600580312 |
0.415 |
|
| 1969 |
Zimmerman HE, Binkley RW, Givens RS, Grunewald GL, Sherwin MA. Mechanistic and exploratory organic photochemistry. XLIV. The barrelene to semibullvalene transformation. Correlation of excited-state potential energy surfaces with reactivity Journal of the American Chemical Society. 91: 3316-3323. DOI: 10.1021/Ja01040A037 |
0.595 |
|
| 1969 |
Zimmerman HE, Grunewald GL, Paufler RM, Sherwin MA. Synthesis and physical properties of barrelene, a unique Moebius-like molecule Journal of the American Chemical Society. 91: 2330-2338. DOI: 10.1021/Ja01037A024 |
0.459 |
|
| 1969 |
Zimmerman HE, Binkley RW, Givens RS, Grunewald GL, Sherwin MA. The barrelene to semibullvalene transformation. Correlation of excited-state potential energy surfaces with reactivity. Mechanistic and exploratory organic photochemistry. XLIV Journal of the American Chemical Society. 91: 3316-3323. |
0.451 |
|
| 1966 |
Zimmerman HE, Grunewald GL. The Chemistry of Barrelene. III. A Unique Photoisomerization to Semibullvalene Journal of the American Chemical Society. 88: 183-184. DOI: 10.1021/Ja00953A045 |
0.431 |
|
| 1964 |
Zimmerman HE, Grunewald GL. The Chemistry of Barrelene. II.1A Remarkable Transformation to Naphthalene Derivatives Journal of the American Chemical Society. 86: 1434-1436. DOI: 10.1021/Ja01061A033 |
0.443 |
|
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