Synthesis of N-[3′-(acetylthio)alkanoyl] and N-[3′ -mercaptoalkanoyl]-4-α(s)-(phenylmethyl) pyroglutamic acids and prolines as potent ACE inhibitors

Medicinal Chemistry Research

Volumn 18, Issue 7, 2009, Pages 566-578

  Panday, Sharad Kumar ^a   Dikshit, Madhu ^b   Dikshit, Dinesh Kumar ^b  

^a M J P ROHILKHAND UNIVERSITY   (India)

^b CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

ACE inhibitors; Captopril; Li enolate; N Acylation; Pyroglutamate

Indexed keywords

2 N [3' (ACETYLTHIO) 1' OXOPROPYL] 4 ALPHA (PHENYLMETHYL) PYROGLUTAMIC ACID; 2 N [3' (ACETYLTHIO) 2' METHYL 1' OXOPROPYL 4 ALPHA (PHENYLMETHYL) PROLINE; 2 N [3' (ACETYLTHIO) 2' METHYL 1'OXOPROPYL] 4 ALPHA (PHENYLMETHYL) PYROGLUTAMIC ACID; 2 N [3' MERCAPTO 1' OXOPROPYL] 4 ALPHA (PHENYLMETHYL) PYROGLUTAMIC ACID; 2 N [3' MERCAPTO 2' METHYL 1' OXOPROPYL] 4' ALPHA (PHENYLMETHYL) PYROGLUTAMIC ACID; 3 (ACETYLTHIO) 2 METHYLPROPIONYL CHLORIDE; 3 (ACETYLTHIO) PROPIONYL CHLORIDE; 4 ALPHA (PHENYLMETHYL) PYROGLUTAMATE; CAPTOPRIL; DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; N [3' (ACETYLTHIO) 2' METHYL 1' OXOPROPYL] 2,4 BIS(PHENYLMETHYL)PYROGLUTAMIC ACID; N [3' (ACETYLTHIO)ALKANOYL] 4 ALPHA (PHENYLMETHYL) PYROGLUTAMIC ACID; N [3' MERCAPTO 2' METHYL 1' OXOPROPYL] 2,4 BIS (PHENYLMETHYL) PYROGLUTAMIC ACID; N [3' MERCAPTOALKANOYL] 4 ALPHA (PHENYLMETHYL) PYROGLUTAMIC ACID; PROLINE DERIVATIVE; PYROGLUTAMIC ACID; PYROGLUTAMIC ACID DERIVATIVE; TERT BUTYL 2 4 ALPHA (PHENYLMETHYL) PROLINATE; TERT BUTYL 2 4 ALPHA (PHENYLMETHYL) PYROGLUTAMATE; TERT BUTYL 2 N [3' (ACETYLTHIO) 1' OXOPROPYL] 4 ALPHA (PHENYLMETHYL) PYROGLUTAMATE; TERT BUTYL 2 N [3' (ACETYLTHIO) 2' METHYL 1' OXOPROPYL] 4 ALPHA (PHENYLMETHYL) PROLINATE; TERT BUTYL 2 N [3' (ACETYLTHIO) 2' METHYL 1'OXOPROPYL] 4 ALPHA (PHENYLMETHYL) PYROGLUTAMATE; TERT BUTYL 2,4 BIS(PHENYLMETHYL)PYROGLUTAMATE; TERT BUTYL N [3' (ACETYLTHIO) 2' METHYL 1' OXOPROPYL] 2,4 BIS(PHENYLMETHYL)PYROGLUTAMATE; UNCLASSIFIED DRUG;

ACYLATION; ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG SYNTHESIS; ENZYME INHIBITION; IN VITRO STUDY; IN VIVO STUDY; NONHUMAN; RAT;

EID: 70349263512     PISSN: 10542523     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00044-008-9150-z     Document Type: Article

References (33)

1. EN Alexandrou M Liakopoulou-Kyriakides 1990 Inhibition of angiotensin-converting enzyme by l-alanyl-4 or 5-substituted l-prolines and their N-alpha-phosphoryl-derivatives Biochem Int 21 2 271 278 2403366 1:CAS:528:DyaK3cXmtVOhsbk%3D
2. J Biollaz M Burnier GA Turini DB Brunner M Porchet HJ Gomez KH Jones F Ferber WB Abrams H Gavras HR Bruner 1981 Three new long acting angiotensin-converting enzyme inhibitors; relationship between plasma converting enzyme activity and pressor response to angiotensin-I Clin Pharmacol Ther 29 665 670 6260419 1:CAS:528:DyaL3MXktlGksrs%3D
3. Caubert V, Langlois N (2006) Studies toward the synthesis of salinosporamide A, a potent proteasome inhibitor Tetrahedron Lett 47:4473-4475. doi: 10.1016/j.tetlet.2006.04.070 (and references cited therein)
4. X Chen D-M Du W-T Hua 2002 Pyroglutamic acid: a versatile building block in asymmetric synthesis Tetrahedron Asymmetry 13 43 46 10.1016/S0957-4166(02) 00052-6 10.1016/S0957-4166(02)00052-6 1:CAS:528:DC%2BD38XisVyqurg%3D (Pubitemid 34219292)
5. DW Cushman HS Cheung 1971 Spectroscopic assay and properties of the angiotensin-converting enzyme of rabbit lung Biochem Pharmacol 20 1637 1648 10.1016/0006-2952(71)90292-9 10.1016/0006-2952(71)90292-9 1:CAS:528: DyaE3MXltVGgs78%3D
6. Cushman DW, Ondetti MA (1980) Inhibitors of angiotensin-converting enzyme. In: Ellis GP, West GB (eds) Progress in Medical Chemistry. Elsevier/North Holland, Amsterdam, pp 17-41
7. Dikshit DK, Panday SK (1992) Aldol reactions of pyroglutamates: chiral synthesis of 4-α(S)- and 4-β(R)-arylmethyl pyroglutamates. J Org Chem 57:1920-1924. doi: 10.1021/jo00032a056 (and references cited therein)
8. DK Dikshit A Maheshwari SK Panday 1995 Self reproduction of chirality in pyroglutamates; Reactions at α-position with electrophiles Tetrahedron Lett 36 6131 6134 10.1016/0040-4039(95)01160-J 10.1016/0040-4039(95)01160-J 1:CAS:528:DyaK2MXnslWrtrg%3D
9. Herdeis C, Kelm B (2003). A stereoselective synthesis of 3-substituted(S)-pyroglutamic and glutamic acids via OBO ester derivatives. Tetrahedron 59:217-219. doi: 10.1016/S0040-4020(02)01490-4 (and references cited therein)
10. K Imaki S Sakuyama T Okada M Toda M Hayashi T Miyamoto A Kawasaki T Okegawa 1981 Potent orally active inhibitors of angiotensin-converting enzyme (ACE) Chem Pharm Bull (Tokyo) 29 2210 2214 1:CAS:528:DyaL38XmsFSh
11. J Krapcho C Turk DW Cushman JR Powell JM Deforrest ER Spitzmiller DS Karanewsky M Duggan G Rovnyak J Schwartz S Natrajan JD Godfrey DE Ryono R Neubeck KS Atwal EW Petrillo Jr 1988 Angiotensin-converting enzyme inhibitors, mercaptan, carboxyalkyl dipeptide and phosphinic acid inhibitors incorporating 4-substituted prolines J Med Chem 31 6 1148 1160 10.1021/jm00401a014 2836590 10.1021/jm00401a014 1:CAS:528:DyaL1cXit1ais7s%3D
12. Ksander GM (1984) Abstracts, 19th National Med. Chem. Symposium, Tucson, AZ, June 17-21, 1984, p 20
13. Laragh JH (1980) In: Case DB (ed) Captopril and hypertension. Plenum, New York, p 173
14. C Najera M Yus 1999 Pyroglutamic acid: a versatile building block in asymmetric Synthesis Tetrahedron Asymmetry 10 2245 2303 10.1016/S0957-4166(99) 00213-X 10.1016/S0957-4166(99)00213-X 1:CAS:528:DyaK1MXltlKksrs%3D (Pubitemid 29371969)
15. Y Ohfune M Tomita 1982 Total synthesis of (-)-domoic acid. A revision of original structure J Am Chem Soc 104 3511 3513 10.1021/ja00376a048 10.1021/ja00376a048 1:CAS:528:DyaL38Xkt1ems7Y%3D
16. T Ohta A Hosoi S Nozoe 1988 Stereoselective hydroxylation of N-carbamoyl-l-pyroglutamate. Synthesis of (-)-bulgecinine Tetrahedron Lett 29 329 332 10.1016/S0040-4039(00)80087-8 10.1016/S0040-4039(00)80087-8 1:CAS:528:DyaL1cXlslSrsL0%3D
17. Ondetti MA, Cushman DW (1981) In: Soffer RL (ed) Biochemical regulation of blood pressure. Wiley, New York, pp 165-204
18. MA Ondetti DW Cushman 1982 Enzymes of the rennin-angiotensin system and their inhibitors Ann Rev Biochem 51 283 308 10.1146/annurev.bi.51.070182.001435 6287916 10.1146/annurev.bi.51.070182.001435 1:CAS:528:DyaL38Xks1KntrY%3D
19. MA Ondetti DW Cushman 1984 Angiotensin-converting enzyme inhibitors: biochemical properties and biological actions CRC Crit Rev Biochem 16 381 411 10.3109/10409238409108720 6094098 10.3109/10409238409108720 1:CAS:528: DyaL2cXmt1WqsLk%3D
20. SK Panday N Langlois 1997 An efficient straight forward synthesis of (-)-bulgecinine Syn Comm 27 8 1373 1384 10.1080/00397919708006067 10.1080/00397919708006067 1:CAS:528:DyaK2sXisVKntLc%3D
21. AA Patchett EW Harris EW Tristram MJ Wyvratt MT Wu D Taub ER Peterson TJ Ikeler JL Broeke LG Payne DL Ondeyka ED Thorsett WJ Greenlee NS Lohr RD Hoffsommer H Joshua WV Ruyle JW Rothroch SD Aster AL Maycock FM Robinson R Hirschmann CS Sweet EM Ulm DM Gross TC Vassil CA Stone 1980 A new class of angiotensin-converting enzyme inhibitors Nature 288 280 283 6253826 10.1038/288280a0 1:CAS:528:DyaL3MXktlGhtLY%3D (Pubitemid 11165879)
22. JS Peterson G Fels H Rapoport 1984 Chirospecific synthesis of (+) and (-)-anatoxin a J Am Chem Soc 106 4539 4547 10.1021/ja00328a040 10.1021/ja00328a040
23. EW Petrillo Jr MA Ondetti 1982 Angiotensin-converting enzyme inhibitors: medicinal chemistry and biological actions Med Res Rev 2 1 41 10.1002/med.2610020103 6287131 10.1002/med.2610020103 1:CAS:528: DyaL38XktFKnt7Y%3D (Pubitemid 12051910)
24. D Potts PJ Stevenson N Thomson 2000 Expedient synthesis of (+)-trans-5-allyl hexahydroindolizidin-3-one Tetrahedron Lett 41 275 278 10.1016/S0040-4039(99)02034-1 10.1016/S0040-4039(99)02034-1 1:CAS:528: DC%2BD3cXkt1ajsg%3D%3D
25. B Rigo C Lespagnol M Pauly 1988 Studies on pyrrolidinones; synthesis of N-acyl pyroglutamic esters with bactericide and fungicide properties J Heterocycl Chem 25 1 49 59 10.1002/jhet.5570250108 1:CAS:528:DyaL1cXlslSrsLo%3D
26. EM Smith GF Swiss Neustadt BR Gold Sommer JA EH AD Brown PJS Chiu R Moran EJ Sybertz TJ Baum 1988 Synthesis and pharmacological activity of angiotensin-converting enzyme inhibitors: N-(mercaptoalkanoyl)-4-substituted-(S) -prolines Med Chem 31 4 875 885 10.1021/jm00399a033 10.1021/jm00399a033 1:CAS:528:DyaL1cXktlyhs7s%3D
27. Smith EM, Swiss GF, Neustadt BR, McNamara P, Gold EH, Sybertz EJ, Baum T (1989) Angiotensin-converting enzyme inhibitors: spirapril and related compounds. J Med Chem 32:1600-1606. doi: 10.1021/jm00127a033 (and references cited therein)
28. JT Suh JA Skiles BE Williams RD Youssefyeh H Jones B Love ES Neiss A Schwab WS Mann A Khandwala PS Wolf MA Weinryb 1985 Angiotensin converting enzyme inhibitors. New orally active anti hypertensive (mercaptoalkanoyl) and [(acylthio) alkanoyl] glycine derivatives J Med Chem 28 1 57 66 10.1021/jm00379a013 2981324 10.1021/jm00379a013 1:CAS:528:DyaL2MXnt1equg%3D%3D (Pubitemid 15156297)
29. JK Thottahil JL Moniot RH Mueller MKY Wong TPJ Kissick 1986 Conversion of l-pyroglutamic acid to 4-alkyl substituted-l-prolines: the synthesis of trans-4-cyclohexyl-l-proline J Org Chem 51 3140 3143 10.1021/jo00366a011 10.1021/jo00366a011
30. Wiecek A, Grzeszczak W (1986) Poly Arch Med Wewn 76(5-6/11-12):291-297
31. MA Wyratt AA Patchett 1985 Recent developments in the design of angiotensin-converting enzyme inhibitors Med Res Rev 5 483 531 10.1002/med.2610050405 10.1002/med.2610050405
32. MJ Wyvratt EW Tristram TJ Ikeler NS Lohr H Joshua JP Springer BH Arison AA Patchett 1984 Chirality in drug research J Org Chem 49 2816 2819 10.1021/jo00189a036 10.1021/jo00189a036 1:CAS:528:DyaL2cXksFGmsLY%3D
33. X Zhang W Jiang AC Schmitt 2001 A convenient and versatile synthesis of 6,5 and 7,5-fused bicyclic lactams as peptidomimetics Tetrahedron Lett 42 4943 4945 10.1016/S0040-4039(01)00909-1 1:CAS:528:DC%2BD3MXkvFyrtbc%3D (Pubitemid 32607367)