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Ralph F. Hirschmann, Ph.D. - Publications

Affiliations: 
1950-1987 Chemistry Merck, Semoy, Centre-Val de Loire, France 
 1988-2009 Chemistry University of Pennsylvania, Philadelphia, PA, United States 
Area:
organic, medicinal and bioorganic chemistry
Website:
https://www.sas.upenn.edu/news/death-renowned-penn-chemist-ralph-f-hirschmann-1922-2009

64 high-probability publications. We are testing a new system for linking publications to authors. You can help! If you notice any inaccuracies, please sign in and mark papers as correct or incorrect matches. If you identify any major omissions or other inaccuracies in the publication list, please let us know.

Year Citation  Score
2011 Smith AB, Charnley AK, Hirschmann R. Pyrrolinone-based peptidomimetics. "Let the enzyme or receptor be the judge". Accounts of Chemical Research. 44: 180-93. PMID 21175156 DOI: 10.1021/Ar1001186  0.403
2010 Smith AB, Xiong H, Charnley AK, Brenner M, Mesaros EF, Kenesky CS, Di Costanzo L, Christianson DW, Hirschmann R. Design, synthesis, and structural analysis of D,L-mixed polypyrrolinones. 2. Macrocyclic hexapyrrolinones. Organic Letters. 12: 2994-7. PMID 20518572 DOI: 10.1021/Ol101008Y  0.359
2010 Smith AB, Wang W, Charnley AK, Carroll PJ, Kenesky CS, Hirschmann R. Design, synthesis, and structural analysis of D,L-mixed polypyrrolinones. 1. From nonpeptide peptidomimetics to nanotubes. Organic Letters. 12: 2990-3. PMID 20518540 DOI: 10.1021/Ol101007N  0.302
2010 SMITH ABI, BENOWITZ AB, FAVOR DA, SPRENGELER PA, HIRSCHMANN R. ChemInform Abstract: A Second-Generation Synthesis of Scalemic 3,5,5-Trisubstituted Pyrrolin-4-ones: Incorporation of Functionalized Amino Acid Side- Chains. Cheminform. 28: no-no. DOI: 10.1002/CHIN.199736224  0.734
2006 Mowery BP, Prasad V, Kenesky CS, Angeles AR, Taylor LL, Feng JJ, Chen WL, Lin A, Cheng FC, Smith AB, Hirschmann R. Catechol: A minimal scaffold for non-peptide peptidomimetics of the i + 1 and i + 2 positions of the beta-turn of somatostatin. Organic Letters. 8: 4397-400. PMID 16986909 DOI: 10.1021/Ol061488X  0.355
2005 Neelamkavil S, Arison B, Birzin E, Feng JJ, Chen KH, Lin A, Cheng FC, Taylor L, Thornton ER, Smith AB, Hirschmann R. Replacement of Phe6, Phe7, and Phe11 of D-Trp8-somatostatin-14 with L-pyrazinylalanine. Predicted and observed effects on binding affinities at hSST2 and hSST4. An unexpected effect of the chirality of Trp8 on NMR spectra in methanol. Journal of Medicinal Chemistry. 48: 4025-30. PMID 15943475 DOI: 10.1021/Jm058184L  0.347
2005 Angeles AR, Neagu I, Birzin ET, Thornton ER, Smith AB, Hirschmann R. Synthesis and binding affinities of novel SRIF-mimicking beta-D-glucosides satisfying the requirement for a pi-cloud at C1. Organic Letters. 7: 1121-4. PMID 15760154 DOI: 10.1021/Ol050119I  0.374
2005 Neelamkavil S, Mowery BP, Thornton ER, Smith AB, Hirschmann R. A practical synthesis of Nalpha-Fmoc-L-pyrazinylalanine via Schöllkopf's chiral auxiliary. The Journal of Peptide Research : Official Journal of the American Peptide Society. 65: 139-42. PMID 15686544 DOI: 10.1111/J.1399-3011.2005.00197.X  0.333
2005 Smith AB, Charnley AK, Mesaros EF, Kikuchi O, Wang W, Benowitz A, Chu CL, Feng JJ, Chen KH, Lin A, Cheng FC, Taylor L, Hirschmann R. Design, synthesis, and binding affinities of pyrrolinone-based somatostatin mimetics. Organic Letters. 7: 399-402. PMID 15673249 DOI: 10.1021/Ol0476974  0.409
2004 Abrous L, Jokiel PA, Friedrich SR, Hynes J, Smith AB, Hirschmann R. Novel chimeric scaffolds to extend the exploration of receptor space: hybrid beta-D-glucose-benzoheterodiazepine structures for broad screening. Effect of amide alkylation on the course of cyclization reactions. The Journal of Organic Chemistry. 69: 280-302. PMID 14725439 DOI: 10.1021/Jo0352068  0.672
2003 Smith AB, Cho YS, Pettit GR, Hirschmann R. Design, synthesis, and evaluation of azepine-based cryptophycin mimetics Tetrahedron. 59: 6991-7009. DOI: 10.1016/S0040-4020(03)00857-3  0.328
2001 Abrous L, Hynes J, Friedrich SR, Smith AB, Hirschmann R. Design and synthesis of novel scaffolds for drug discovery: hybrids of beta-D-glucose with 1,2,3,4-tetrahydrobenzo[e][1,4]diazepin-5-one, the corresponding 1-oxazepine, and 2- and 4-pyridyldiazepines. Organic Letters. 3: 1089-92. PMID 11277802 DOI: 10.1021/Ol015698F  0.664
2001 Hirschmann R, Ducry L, Smith AB. Development of an efficient, regio- and stereoselective route to libraries based on the beta-D-glucose scaffold. The Journal of Organic Chemistry. 65: 8307-16. PMID 11101390 DOI: 10.1021/Jo001099V  0.34
2000 Liu J, Underwood DJ, Cascieri MA, Rohrer SP, Cantin LD, Chicchi G, Smith AB, Hirschmann R. Synthesis of a substance P antagonist with a somatostatin scaffold: factors affecting agonism/antagonism at GPCRs and the role of pseudosymmetry. Journal of Medicinal Chemistry. 43: 3827-31. PMID 11052787 DOI: 10.1021/Jm000316H  0.748
2000 Smith AB, Liu H, Okumura H, Favor DA, Hirschmann R. Synthesis of polypyrrolinones on solid support. Organic Letters. 2: 2041-4. PMID 10891225 DOI: 10.1021/Ol005931U  0.74
2000 Schiller PW, Berezowska I, Nguyen TMD, Schmidt R, Lemieux C, Chung NN, Falcone-Hindley ML, Yao W, Liu J, Iwama S, Smith AB, Hirschmann RF. Novel ligands lacking a positive charge for the δ- and μ-opioid receptors Journal of Medicinal Chemistry. 43: 551-559. PMID 10691681 DOI: 10.1021/Jm990461Z  0.742
2000 Smithrud DB, Benkovic PA, Benkovic SJ, Roberts V, Liu J, Neagu I, Iwama S, Phillips BW, Smith AB, Hirschmann R. Cyclic peptide formation catalyzed by an antibody ligase Proceedings of the National Academy of Sciences of the United States of America. 97: 1953-1958. PMID 10688882 DOI: 10.1073/Pnas.040534397  0.739
1999 Soli ED, Manoso AS, Patterson MC, DeShong P, Favor DA, Hirschmann R, Smith AB. Azide and Cyanide Displacements via Hypervalent Silicate Intermediates. The Journal of Organic Chemistry. 64: 3171-3177. PMID 11674417 DOI: 10.1021/Jo982302D  0.734
1999 Smith AB, Favor DA, Sprengeler PA, Guzman MC, Carroll PJ, Furst GT, Hirschmann R. Molecular modeling, synthesis, and structures of N-methylated 3,5-linked pyrrolin-4-ones toward the creation of a privileged nonpeptide scaffold. Bioorganic & Medicinal Chemistry. 7: 9-22. PMID 10199652 DOI: 10.1016/S0968-0896(98)00234-X  0.743
1999 Smith AB, Benowitz AB, Sprengeler PA, Barbosa J, Guzman MC, Hirschmann R, Schweiger EJ, Bolin DR, Nagy Z, Campbell RM, Cox DC, Olson GL. Design and Synthesis of a Competent Pyrrolinone−Peptide Hybrid Ligand for the Class II Major Histocompatibility Complex Protein HLA-DR1 Journal of the American Chemical Society. 121: 9286-9298. DOI: 10.1021/Ja991251E  0.328
1998 Hirschmann R, Hynes J, Cichy-Knight MA, van Rijn RD, Sprengeler PA, Spoors PG, Shakespeare WC, Pietranico-Cole S, Barbosa J, Liu J, Yao W, Rohrer S, Smith AB. Modulation of receptor and receptor subtype affinities using diastereomeric and enantiomeric monosaccharide scaffolds as a means to structural and biological diversity. A new route to ether synthesis. Journal of Medicinal Chemistry. 41: 1382-91. PMID 9554871 DOI: 10.1021/Jm9800346  0.763
1998 Hirschmann R, Yao W, Arison B, Maechler L, Rosegay A, Sprengeler PA, Smith AB. Synthesis of the first tricyclic homodetic peptide. Use of coordinated orthogonal deprotection to achieve directed ring closure Tetrahedron. 54: 7179-7202. DOI: 10.1016/S0040-4020(98)00354-8  0.411
1997 Hirschmann R, Yager KM, Taylor CM, Witherington J, Sprengeler PA, Phillips BW, Moore W, Smith AB. Phosphonate Diester and Phosphonamide Synthesis. Reaction Coordinate Analysis by 31P NMR Spectroscopy: Identification of Pyrophosphonate Anhydrides and Highly Reactive Phosphonylammonium Salts1 Journal of the American Chemical Society. 119: 8177-8190. DOI: 10.1021/Ja962465O  0.323
1997 Smith AB, Benowitz AB, Favor DA, Sprengeler PA, Hirschmann R. A second-generation synthesis of scalemic 3,5,5-trisubstituted pyrrolin-4-ones: Incorporation of functionalized amino acid side-chains Tetrahedron Letters. 38: 3809-3812. DOI: 10.1016/S0040-4039(97)00752-1  0.751
1996 Smith AB, Knight SD, Sprengeler PA, Hirschmann R. The design and synthesis of 2,5-linked pyrrolinones. A potential non-peptide peptidomimetic scaffold. Bioorganic & Medicinal Chemistry. 4: 1021-34. PMID 8831973 DOI: 10.1016/0968-0896(96)00094-6  0.39
1996 Hirschmann R, Yao W, Cascieri MA, Strader CD, Maechler L, Cichy-Knight MA, Hynes J, van Rijn RD, Sprengeler PA, Smith AB. Synthesis of potent cyclic hexapeptide NK-1 antagonists. Use of a minilibrary in transforming a peptidal somatostatin receptor ligand into an NK-1 receptor ligand via a polyvalent peptidomimetic. Journal of Medicinal Chemistry. 39: 2441-8. PMID 8691440 DOI: 10.1021/Jm960281E  0.664
1996 Hirschmann R, Yao W, Arison B, Maechler L, Rosegay A, Sprengeler PA, Smith AB. The first synthesis of a tricyclic homodetic peptide employing coordinated orthogonal protection Tetrahedron Letters. 37: 5637-5640. DOI: 10.1016/0040-4039(96)01221-X  0.396
1995 Smith AB, Akaishi R, Jones DR, Keenan TP, Guzman MC, Holcomb RC, Sprengeler PA, Wood JL, Hirschmann R, Holloway MK. Design and synthesis of nonpeptide peptidomimetic inhibitors of renin. Biopolymers. 37: 29-53. PMID 7880965 DOI: 10.1002/Bip.360370106  0.329
1995 Hirschmann R, Yager KM, Taylor CM, Moore W, Sprengeler PA, Witherington J, Phillips BW, Smith ABI. Phosphonyltriethylammonium Salts : Novel Reactive Species For The Synthesis Of Phosphonate Esters And Phosphononamides Journal of the American Chemical Society. 117: 6370-6371. DOI: 10.1021/Ja00128A032  0.308
1995 Hirschmann R, Hynes J, Spoors P, Smith AB. Chemoselective monoalkylation of 5-trifluoroacetamido- and 5-acetamido-1-pentanol derivatives via N,O-bisdeprotonation. Quantitation of evolved H2 as a probe of anion formation Tetrahedron Letters. 36: 2373-2376. DOI: 10.1016/0040-4039(95)00280-P  0.6
1994 Hirschmann R, Smith AB, Taylor CM, Benkovic PA, Taylor SD, Yager KM, Sprengeler PA, Benkovic SJ. Peptide synthesis catalyzed by an antibody containing a binding site for variable amino acids. Science (New York, N.Y.). 265: 234-7. PMID 8023141 DOI: 10.1126/Science.8023141  0.335
1994 Smith AB, Pasternak A, Yokoyama A, Hirschmann R. Enantioretentive alkylation of oxazolidinone aluminum enolates with epoxides: Preparation of uncoded homoserine analogs Tetrahedron Letters. 35: 8977-8980. DOI: 10.1016/0040-4039(94)88404-8  0.374
1993 Lender A, Yao W, Sprengeler PA, Spanevello RA, Furst GT, Hirschmann R, Smith AB. Design and synthesis of sulfur-free cyclic hexapeptides which contain the RGD sequence and bind to the fibrinogen GP IIb/IIIa receptor. A conformation-based correlation between propensity for imide formation and receptor affinity. International Journal of Peptide and Protein Research. 42: 509-17. PMID 8307682 DOI: 10.1111/J.1399-3011.1993.Tb00358.X  0.411
1993 Hirschmann R, Nicolaou KC, Pietranico S, Leahy EM, Salvino J, Arison B, Cichy MA, Spoors PG, Shakespeare WC. De novo design and synthesis of somatostatin non-peptide peptidomimetics utilizing .beta.-D-glucose as a novel scaffolding Journal of the American Chemical Society. 115: 12550-12568. DOI: 10.1021/Ja00079A039  0.39
1993 Hirschmann R, Sprengeler PA, Kawasaki T, Leahy JW, Shakespeare WC, Smith AB. The versatile steroid nucleus: Design and synthesis of a peptidomimetic employing this novel scaffold. Tetrahedron. 49: 3665-3676. DOI: 10.1016/S0040-4020(01)90222-4  0.356
1992 Hirschmann R. The cortisone era: aspects of its impact. Some contributions of the Merck Laboratories. Steroids. 57: 579-592. PMID 1481224 DOI: 10.1016/0039-128X(92)90012-X  0.304
1992 Smith AB, Keenan TP, Holcomb RC, Sprengeler PA, Guzman MC, Wood JL, Carroll PJ, Hirschmann R. Design, synthesis, and crystal structure of a pyrrolinone-based peptidomimetic possessing the conformation of a .beta.-strand: potential application to the design of novel inhibitors of proteolytic enzymes Journal of the American Chemical Society. 114: 10672-10674. DOI: 10.1021/Ja00052A093  0.31
1992 Hirschmann R, Nicolaou K, Pietranico S, Salvino J, Leahy EM, Sprengeler PA, Furst G, Smith AB, Strader CD, Cascieri MA, Candelore MR, Donaldson C, Vale W, Maechler L. Nonpeptidal peptidomimetics with a β-D-glucose scaffolding. A partial somatostatin agonist bearing a close structural relationship to a potent, selective substance P antagonist Journal of the American Chemical Society. 114: 9217-9218. DOI: 10.1021/Ja00049A081  0.329
1991 Spanevello RA, Hirschmann R, Raynor K, Reisine T, Nutt RF. Synthesis of novel, highly potent cyclic-hexapeptide analogs of somatostatin. Potential application of orthogonal protection for affinity chromatography Tetrahedron Letters. 32: 4675-4678. DOI: 10.1016/S0040-4039(00)92279-2  0.402
1990 Wood JL, Jones DR, Hirschmann R, Smith AB. A versatile, efficient synthesis of (-)-(2S, 3R, 4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane, the abbott pseudodipeptidyl insert Tetrahedron Letters. 31: 6329-6330. DOI: 10.1016/S0040-4039(00)97055-2  0.304
1983 Bolhofer WA, Deana AA, Habecker CN, Hoffman JM, Gould NP, Pietruszkiewicz AM, Prugh JD, Torchiana ML, Cragoe EJ, Hirschmann R. Inhibitors of gastric acid secretion: antisecretory 2-pyridylurea derivatives. Journal of Medicinal Chemistry. 26: 538-544. PMID 6834386 DOI: 10.1021/Jm00358A015  0.325
1983 Hoffman JM, Habecker CN, Pietruszkiewicz AM, Bolhofer WA, Cragoe EJ, Torchiana ML, Hirschmann R. A deuterium isotope effect on the inhibition of gastric secretion by N,N-dimethyl-N'-[2-(diisopropylamino)ethyl]-N'-(4,6-dimethyl-2-pyridyl)urea. Synthesis of metabolites. Journal of Medicinal Chemistry. 26: 1650-1653. PMID 6631919 DOI: 10.1021/Jm00365A020  0.316
1981 Nutt RF, Holly FW, Homnick C, Hirschmann R, Veber DF, Arison BH. Synthesis of thyrotropin-releasing hormone analogues with selective central nervous system effects. Journal of Medicinal Chemistry. 24: 692-698. PMID 6788956 DOI: 10.1021/Jm00138A010  0.383
1980 Baldwin JJ, Engelhardt EL, Hirschmann R, Ponticello GS, Atkinson JG, Wasson BK, Sweet CS, Scriabine A. Heterocyclic analogues of the antihypertensive beta-adrenergic blocking agent (S)-2-[3-(ter-butylamino)-2-hydroxypropoxy]-3-cyanopyridine. Journal of Medicinal Chemistry. 23: 65-70. PMID 6102151 DOI: 10.1021/Jm00175A012  0.339
1978 Freidinger RM, Hirschmann R, Veber DF. Titanium(III) as a selective reducing agent for nitroarginyl peptides: synthesis of arginine vasotocin Journal of Organic Chemistry. 10: 4800-4803. DOI: 10.1021/Jo00419A019  0.326
1978 Saari WS, Freedman MB, Hartman RD, King SW, Raab AW, Randall WC, Engelhardt EL, Hirschmann R, Rosegay A, Ludden CT, Scriabine A. Synthesis And Antihypertensive Activity Of Some Ester Progenitors Of Methyldopa Cheminform. 9. DOI: 10.1002/Chin.197851161  0.344
1978 Veber DF, Paleveda WJJ, Lee YC, Hirschmann R. Isonicotinyloxycarbonyl A Novel Amino Protecting Group For Peptide Synthesis Cheminform. 9. DOI: 10.1002/Chin.197803360  0.35
1977 Veber DF, Paleveda WJ, Lee YC, Hirschmann R. Isonicotinyloxycarbonyl, a novel amino protecting group for peptide synthesis. The Journal of Organic Chemistry. 42: 3286-8. PMID 20489 DOI: 10.1021/Jo00440A018  0.35
1977 Remy DC, Rittle KE, Hunt CA, Anderson PS, Arison BH, Engelhardt EL, Hirschmann R, Clineschmidt BV, Lotti VJ, Bunting PR, Ballentine RJ, Papp NL, Flataker L, Witoslawski JJ, Stone CA. Synthesis And Stereospecific Antipsychotic Activity Of (-)-1-Cyclopropylmethyl-4-(3-Trifluoromethylthio-5H-Dibenzo(A,D)Cyclohepten-5-Ylidene)Piperidine Cheminform. 8. DOI: 10.1002/Chin.197749245  0.308
1976 Veber DF, Strachan RG, Bergstrand SJ, Holly FW, Homnick CG, Hirschmann R, Torchiana ML, Saperstein R. Nonreducible cyclic analogues of somatostatin Journal of the American Chemical Society. 98: 2367-2369. DOI: 10.1021/Ja00424A078  0.354
1971 Hirschmann R, Schwam H, Strachan RG, Schoenewaldt EF, Barkemeyer H, Miller SM, Conn JB, Garsky V, Veber DF, Denkewalter RG. Controlled synthesis of peptides in aqueous medium. VIII. Preparation and use of novel .alpha.-amino acid N-carboxyanhydrides Journal of the American Chemical Society. 93: 2746-2754. PMID 5573721 DOI: 10.1021/Ja00740A027  0.345
1971 Dewey RS, Schoenewaldt EF, Joshua H, Paleveda WJ, Schwam H, Barkemeyer H, Arison BH, Veber DF, Strachan RG, Milkowski J, Denkewalter RG, Hirschmann R. The synthesis of peptides in aqueous medium. VII. The preparation and use of 2,5-thiazolidinediones in peptide synthesis. The Journal of Organic Chemistry. 36: 49-59. PMID 5543046 DOI: 10.1021/Jo00800A013  0.341
1969 Veber DF, Hirschmann R, Denkewalter RG. Synthesis of peptides in aqueous medium. VI. Synthesis of an unsymmetrical cystine peptide fragment of insulin Journal of Organic Chemistry. 34: 753-755. DOI: 10.1021/Jo01255A066  0.324
1968 Veber DF, Milkowski JD, Denkewalter RG, Hirschmann R. The synthesis of peptides in aqueous medium. IV. A novel protecting group for cysteine. Tetrahedron Letters. 9: 3057-3058. PMID 5651011 DOI: 10.1016/S0040-4039(00)89595-7  0.339
1967 Hirschmann R, Strachan RG, Schwam H, Schoenewaldt EF, Joshua H, Barkemeyer B, Veber DF, Paleveda WJ, Jacob TA, Beesley TE, Denkewalter RG. The controlled synthesis of peptides in aqueous medium. 3. Use of Leuchs' anhydrides in the synthesis of dipeptides. Mechanism and control of side reactions. The Journal of Organic Chemistry. 32: 3415-25. PMID 5622457 DOI: 10.1021/Jo01286A030  0.338
1966 Denkewalter RG, Schwam H, Strachan RG, Beesley TE, Veber DF, Schoenewaldt EF, Barkemeyer H, Paleveda WJ, Jacob TA, Hirschmann R. The Controlled Synthesis of Peptides in Aqueous Medium. I. The Use of α-Amino Acid N-Carboxyanhydrides Journal of the American Chemical Society. 88: 3163-3164. DOI: 10.1021/Ja00965A069  0.344
1964 Strachan RG, Meisinger MAP, Ruyle WV, Hirschmann R, Shen TY. Synthesis Of Indomethacin Metabolites. Journal of Medicinal Chemistry. 7: 799-800. PMID 14262813 DOI: 10.1021/Jm00336A026  0.336
1964 STRACHAN R, STEINBERG NG, TISHLER M, HIRSCHMANN R. SYNTHESIS OF 2'-(2,4-DIFLUOROPHENYL )-11-BETA, Journal of Medicinal Chemistry. 7: 355. PMID 14204976 DOI: 10.1021/Jm00333A024  0.313
1962 Strachan R, Wood J, Hirschmann R. Synthesis and Properties of 4-Methyl-2-oxo-1,2-benzopyran-7-yl β-D-Galactoside (Galactoside of 4-Methylumbelliferone) Journal of Organic Chemistry. 27: 1074-1075. DOI: 10.1021/Jo01050A530  0.317
1962 Hirschmann R, Steinberg NG, Walker R. A General Synthesis of 4,5-Unsaturated 2-Oxasteroids. A Synthesis of 2-Oxacortisol Journal of the American Chemical Society. 84: 1270-1278. DOI: 10.1021/Ja00866A043  0.378
1953 Hiskey CF, Hirschmann R, Wendler NL. REARRANGEMENT OF THE STEROID C/D RINGS. SYNTHESIS OF AN 11-KETO-Δ13(17a)-C-NOR/D-HOMO-STEROID Journal of the American Chemical Society. 75: 5135-5136. DOI: 10.1021/Ja01116A526  0.315
1953 Hirschmann R, Wendler NL. The Structure of the Enol Acetate Derivatives of Steroid 7- and 11-Ketones Journal of the American Chemical Society. 75: 2361-2364. DOI: 10.1021/Ja01106A022  0.317
1951 Hirschmann R, Johnson WS. A New Synthesis of the 6-Methoxy-17-equilenones and Some Stereochemical Considerations Journal of the American Chemical Society. 73: 326-329. DOI: 10.1021/Ja01145A107  0.5
1951 Johnson WS, Gutsche CD, Hirschmann R, Stromberg VL. Structure and Hydrogenation of Key Intermediates in the Equilenin Synthesis1,2 Journal of the American Chemical Society. 73: 322-326. DOI: 10.1021/Ja01145A106  0.426
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