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Volumn 218, Issue 1, 2003, Pages 46-55

Crystal and molecular structures of 4-aryl-1,4-dihydropyrimidines: Novel calcium channel antagonists

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIHYDRO 6 METHYL 5 N METHYL CARBAMOYL 4 (2',4' DICHLOROPHENYL) 2(3H) PYRIMIDINONE; 1,4 DIHYDRO 6 METHYL 5 N METHYL CARBAMOYL 4 (3',4' DICHLOROPHENYL) 2(3H) PYRIMIDINETHIONE; 1,4 DIHYDRO 6 METHYL 5 N METHYL CARBAMOYL 4 (4' METHOXYPHENYL) 2(3H) PYRIMIDINETHIONE; CALCIUM CHANNEL BLOCKING AGENT; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0041808755     PISSN: 00442968     EISSN: None     Source Type: Journal    
DOI: 10.1524/zkri.218.1.46.20771     Document Type: Article
Times cited : (9)

References (38)
  • 1
    • 0015295310 scopus 로고
    • Coronary circulation, systemic resistance and capacitance blood vessels of dogs as effected by BAY a 1040
    • Hirakawa, S.; Ito, H.; Kondo, Y.; Watanabe, I.; Hiei, K.; Banno, S.; Hayase, S.: Coronary circulation, systemic resistance and capacitance blood vessels of dogs as effected by BAY a 1040. Arzneim.-Forsch. 22 (1972) 344-349.
    • (1972) Arzneim.-Forsch. , vol.22 , pp. 344-349
    • Hirakawa, S.1    Ito, H.2    Kondo, Y.3    Watanabe, I.4    Hiei, K.5    Banno, S.6    Hayase, S.7
  • 3
    • 0025274376 scopus 로고
    • Dihydropyrimidine calcium channel blockers. 2-Heterosubstituted 4-Aryl-1,4-dihydro-6-methyl-5-pyrimidinecarboxylic acid esters as potent mimics of Dihydropyridines
    • Atwal, K. S.; Rovnyak, G. C.; Schwartz, J.; Moreland, S.; Hedberg, A.; Gougoutas, J. Z.; Malley, M. F.; Floyd, D. M.: Dihydropyrimidine calcium channel blockers. 2-Heterosubstituted 4-Aryl-1,4-dihydro-6-methyl-5-pyrimidinecarboxylic acid esters as potent mimics of Dihydropyridines. J. Med. Chem. 33 (1990) 1510-1515.
    • (1990) J. Med. Chem. , vol.33 , pp. 1510-1515
    • Atwal, K.S.1    Rovnyak, G.C.2    Schwartz, J.3    Moreland, S.4    Hedberg, A.5    Gougoutas, J.Z.6    Malley, M.F.7    Floyd, D.M.8
  • 4
    • 0025105557 scopus 로고
    • Dihydropyrimidine calcium channel blockers. 3-substituted-4-aryl-1,4-dihydro-6-methyl-5-pyrimidinecarboxylic acid esters as potent mimicks of dihydropyridines
    • Atwal, K. S., Rovnyak, G. C.; Kimball, S. D.; Floyd, D. M.; Moreland, S.; Swanson, B. N.; Gougoutas, J. Z.; Schwartz, J.; Smillie, K. M.; Malley, M. F.: Dihydropyrimidine calcium channel blockers. 3-substituted-4-aryl-1,4-dihydro-6-methyl-5-pyrimidinecarboxylic acid esters as potent mimicks of dihydropyridines. J. Med. Chem. 33 (1990) 2629-2635.
    • (1990) J. Med. Chem. , vol.33 , pp. 2629-2635
    • Atwal, K.S.1    Rovnyak, G.C.2    Kimball, S.D.3    Floyd, D.M.4    Moreland, S.5    Swanson, B.N.6    Gougoutas, J.Z.7    Schwartz, J.8    Smillie, K.M.9    Malley, M.F.10
  • 5
    • 0026759681 scopus 로고
    • Dihydropyrimidine calcium channel blockers. Basic 3-substituted-4-aryl-1,4-dihydropyrimidine-5-carboxylic acid esters. Potent antihypertensive agents
    • Rovnyak, G. C.; Atwal, K. S.; Hedberg, A.; Kimball, S. D.; Moreland, S.; Gougoutas, J. Z.; O'Reilly, B. C.; Schwartz, J.; Malley, M. F.: Dihydropyrimidine calcium channel blockers. Basic 3-substituted-4-aryl-1,4-dihydropyrimidine-5-carboxylic acid esters. Potent antihypertensive agents. J. Med. Chem. 32 (1992) 3254-3263.
    • (1992) J. Med. Chem. , vol.32 , pp. 3254-3263
    • Rovnyak, G.C.1    Atwal, K.S.2    Hedberg, A.3    Kimball, S.D.4    Moreland, S.5    Gougoutas, J.Z.6    O'Reilly, B.C.7    Schwartz, J.8    Malley, M.F.9
  • 6
    • 0034519777 scopus 로고    scopus 로고
    • Biologically active dihydropyrimidones of the Biginelli-type - A literature survey
    • Kappe, C. O.: Biologically active dihydropyrimidones of the Biginelli-type - a literature survey. Eur. J. Med. Chem. 33 (2000) 1043-1052.
    • (2000) Eur. J. Med. Chem. , vol.33 , pp. 1043-1052
    • Kappe, C.O.1
  • 7
    • 0031584880 scopus 로고    scopus 로고
    • Conformational analysis of 4-Aryl-Dihydropyrimidine calcium channel modulators. A comparison of Ab Initio, semiempirical and X-ray Crystallographic studies
    • Kappe, C. O.; Fabian, W. M. F.; Semones, M. A.: Conformational analysis of 4-Aryl-Dihydropyrimidine calcium channel modulators. A comparison of Ab Initio, semiempirical and X-ray Crystallographic studies. Tetrahedron 53 (1997) 2803-2816.
    • (1997) Tetrahedron , vol.53 , pp. 2803-2816
    • Kappe, C.O.1    Fabian, W.M.F.2    Semones, M.A.3
  • 8
    • 0026065919 scopus 로고
    • Dihydropyrimidine calcium channel blockers. 3-carbamoyl-4-aryl-1,2,3,4-tetrahydro-6-methyl-5-pyrimidine carboxylic acid esters as orally effective antihypertensive agents
    • Atwal, K. S.; Swanson, B. N.; Unger, S. E.; Floyd, D. M.; Moreland, S.; Hedberg, A.; O'Reilly, B. C.: Dihydropyrimidine calcium channel blockers. 3-carbamoyl-4-aryl-1,2,3,4-tetrahydro-6-methyl-5-pyrimidine carboxylic acid esters as orally effective antihypertensive agents. J. Med. Chem. 34 (1991) 806-811.
    • (1991) J. Med. Chem. , vol.34 , pp. 806-811
    • Atwal, K.S.1    Swanson, B.N.2    Unger, S.E.3    Floyd, D.M.4    Moreland, S.5    Hedberg, A.6    O'Reilly, B.C.7
  • 9
    • 0042040896 scopus 로고    scopus 로고
    • British patent (1961) 868,030
    • Hull, R.; Swain, G.: British patent (1961) 868,030.
    • Hull, R.1    Swain, G.2
  • 10
    • 0001457151 scopus 로고
    • Two new synthetic substances active against viruses of psittacosis-lymphogranuloma - Trachoma group
    • Hurst, E. W.; Hull, R.: Two new synthetic substances active against viruses of Psittacosis-Lymphogranuloma - Trachoma Group. J. Med. Pharma. Chem. 3 (1961) 215-229.
    • (1961) J. Med. Pharma. Chem. , vol.3 , pp. 215-229
    • Hurst, E.W.1    Hull, R.2
  • 11
    • 0002172891 scopus 로고
    • Synthesis and pharmacological studies of some 1,2,3,4-tetrahydropyrimidine-5-carboxylic acid derivatives
    • Khanina, E. L.; Siliniece, G.; Ozols, J.; Duburs, G.; Kimenis, A.: Synthesis and pharmacological studies of some 1,2,3,4-tetrahydropyrimidine-5-carboxylic acid derivatives. Khim-Farm. Zh. 12 (1978) 72-74.
    • (1978) Khim-Farm. Zh. , vol.12 , pp. 72-74
    • Khanina, E.L.1    Siliniece, G.2    Ozols, J.3    Duburs, G.4    Kimenis, A.5
  • 12
    • 0024477866 scopus 로고
    • Ca2+ channel ligands. Structure-Function relationship of the 1,4-dihydropyridines
    • Triggle, D. J.; Langs, D. A.; Janis, R. A.: Ca2+ channel ligands. Structure-Function relationship of the 1,4-dihydropyridines. Med. Res. Rev. 9 (1989) 123-180.
    • (1989) Med. Res. Rev. , vol.9 , pp. 123-180
    • Triggle, D.J.1    Langs, D.A.2    Janis, R.A.3
  • 14
    • 0026504339 scopus 로고
    • Synthesis and biological evaluation of new 3,4-dihydro-6-methyl-5-N-methyl-carbamoyl-4-(substituted phenyl)-2(1H)pyrimidinones and pyrimidinothiones
    • Sadanandam, Y. S.; Shetty, M. M.; Diwan, P. V.: Synthesis and biological evaluation of new 3,4-dihydro-6-methyl-5-N-methyl-carbamoyl-4-(substituted phenyl)-2(1H)pyrimidinones and pyrimidinothiones. Eur. J. Med. Chem. 27 (1992) 87-92.
    • (1992) Eur. J. Med. Chem. , vol.27 , pp. 87-92
    • Sadanandam, Y.S.1    Shetty, M.M.2    Diwan, P.V.3
  • 15
    • 0004150157 scopus 로고
    • Siemens Analytical X-ray Instruments, Inc. Application Laboratory, Single crystal, Siemens AG, AUT v353, Karlsruhe, Germany
    • Sheldrick, G. M.: SHELXTL-Plus. Revision 4.11N. Siemens Analytical X-ray Instruments, Inc. Application Laboratory, Single crystal, Siemens AG, AUT v353, Karlsruhe, Germany 1990.
    • (1990) SHELXTL-Plus. Revision 4.11N
    • Sheldrick, G.M.1
  • 16
    • 0020909036 scopus 로고
    • PARST. A system of FORTRAN Routines for calculating Molecular structure parameters from results of crystal structure analysis
    • Nardelli, M.: PARST. A system of FORTRAN Routines for calculating Molecular structure parameters from results of crystal structure analysis. Comput. Chem. 7 (1983) 95-98.
    • (1983) Comput. Chem. , vol.7 , pp. 95-98
    • Nardelli, M.1
  • 17
    • 0030172117 scopus 로고    scopus 로고
    • 2.7] trideca-2,4,6-triene-13-carboxylate
    • 2.7] trideca-2,4,6-triene-13-carboxylate. Acta Cryst. C52 (1996) 1496-1499.
    • (1996) Acta Cryst. , vol.C52 , pp. 1496-1499
    • Kettmann, V.1    Svetlik, J.2
  • 18
    • 0031247704 scopus 로고    scopus 로고
    • 2.7] trideca-2,4,6-triene-13-carboxylate
    • 2.7] trideca-2,4,6-triene-13-carboxylate. Acta Cryst. C53 (1997) 1493-1495.
    • (1997) Acta Cryst. , vol.C53 , pp. 1493-1495
    • Kettmann, V.1    Svetlik, J.2
  • 23
  • 24
    • 33845184477 scopus 로고
    • Synthesis of perhydro-1,3-diazine-2-thiones from β-chloroimines
    • Sulmon, P.; De Kimpe, N.; Schamp, N.; Declereq, J. P.: Synthesis of perhydro-1,3-diazine-2-thiones from β-chloroimines. J. Org. Chem. 54 (1988) 2587-2590.
    • (1988) J. Org. Chem. , vol.54 , pp. 2587-2590
    • Sulmon, P.1    De Kimpe, N.2    Schamp, N.3    Declereq, J.P.4
  • 25
    • 0002689030 scopus 로고
    • Crystal structure of 2-thiouracil
    • Tiekink, E. R. T.: Crystal structure of 2-thiouracil. Z. Kristallogr. 187 (1989) 79-84.
    • (1989) Z. Kristallogr. , vol.187 , pp. 79-84
    • Tiekink, E.R.T.1
  • 27
    • 0019296528 scopus 로고
    • Crystal structures of calcium channel antagonists: 2,6-dimethyl-3,5-dicarbomethoxy-4-[2-nitro-, 3-cyano-, 4-(dimethylamino)-, and 2,3,4,5,6-pentafluorophenyl]-1,4-dihydropyridine
    • Triggle, A. M.; Shefter, E.; Triggle, D. J.: Crystal structures of calcium channel antagonists: 2,6-dimethyl-3,5-dicarbomethoxy-4-[2-nitro-, 3-cyano-, 4-(dimethylamino)-, and 2,3,4,5,6-pentafluorophenyl]-1,4-dihydropyridine. J. Med. Chem. 23 (1980) 1442-1445.
    • (1980) J. Med. Chem. , vol.23 , pp. 1442-1445
    • Triggle, A.M.1    Shefter, E.2    Triggle, D.J.3
  • 28
    • 0020058582 scopus 로고
    • Crystal structures and pharmacological activity of calcium channel antagonists: 2,6-Dimethyl-3,5-dicarbomethoxy-4-(unsubstituted, 3-methyl-, 4-methyl-, 3-nitro-, 4-nitro-, and 2,4-dinitrophenyl)-1,4-dihydropyridine
    • Fossheim, R.; Svarteng, K.; Mostad, A.; Romming, C.; Shefter, E.; Triggle, D. J.: Crystal structures and pharmacological activity of calcium channel antagonists: 2,6-dimethyl-3,5-dicarbomethoxy-4-(unsubstituted, 3-methyl-, 4-methyl-, 3-nitro-, 4-nitro-, and 2,4-dinitrophenyl)-1,4-dihydropyridine. J. Med. Chem. 25 (1982) 126-131.
    • (1982) J. Med. Chem. , vol.25 , pp. 126-131
    • Fossheim, R.1    Svarteng, K.2    Mostad, A.3    Romming, C.4    Shefter, E.5    Triggle, D.J.6
  • 29
    • 0042040897 scopus 로고    scopus 로고
    • Crystal structure analysis of 4-R-phenyl-2,6-dimethyl-3,5-N-(dimethyl-carbamoyl)-1,4-dihydropyridines [R=2-nitro (1), 4-methoxy (2) and 3,4-dichloro (3)]
    • Bidya Sagar, M.; Ravikumar, K.; Sadanandam, Y. S.: Crystal structure analysis of 4-R-phenyl-2,6-dimethyl-3,5-N-(dimethyl-carbamoyl)-1,4-dihydropyridines [R=2-nitro (1), 4-methoxy (2) and 3,4-dichloro (3)]. Z. Kristallogr. 213 (1998) 182-190.
    • (1998) Z. Kristallogr. , vol.213 , pp. 182-190
    • Bidya Sagar, M.1    Ravikumar, K.2    Sadanandam, Y.S.3
  • 30
    • 0001501966 scopus 로고    scopus 로고
    • Recemic ethyl 4-(2-fluorophenyl)-2,6,6-trimethyl-5-oxo-1,4-5,6,7,8-hexahydroquinoline-3 -carboxylate
    • Linden, A.; Simsek, R.; Safak, C.: Recemic ethyl 4-(2-fluorophenyl)-2,6,6-trimethyl-5-oxo-1,4-5,6,7,8-hexahydroquinoline-3 -carboxylate. Acta Cryst. C54 (1998) 879-882.
    • (1998) Acta Cryst. , vol.C54 , pp. 879-882
    • Linden, A.1    Simsek, R.2    Safak, C.3
  • 32
    • 0000411512 scopus 로고
    • Crystal and molecular structure of p-methoxy benzyl 2α-methyl-2β-[(R)-acetoxy (methoxy) methyl]-6β -phenoxyacetamidopenam-3α-carboxylate
    • Domiano, P.; Nardelli, M.; Balsamo, A.; Macchia, B.; Macchia, F.: Crystal and molecular structure of p-methoxy benzyl 2α-methyl-2β-[(R)-acetoxy (methoxy) methyl]-6β -phenoxyacetamidopenam-3α-carboxylate. Acta Cryst. B35 (1979) 1363-1372.
    • (1979) Acta Cryst. , vol.B35 , pp. 1363-1372
    • Domiano, P.1    Nardelli, M.2    Balsamo, A.3    Macchia, B.4    Macchia, F.5
  • 35
    • 0042541734 scopus 로고    scopus 로고
    • Crystal and molecular structure of 2,6-dimethyl-3,5-di[N-methyl]-carbamoyl-4-[3,4-methoxy]phenyl-1, 4-dihyfropyridine hemihydrate and 2,6-dimethyl-3,5-di[N-methyl]-carbamoyl-4-[furan]-1,4-dihyfropyridine
    • Bidya Sagar, M.; Ravikumar, K.; Mehdi, S.; Sadanandam Y. S.: Crystal and molecular structure of 2,6-dimethyl-3,5-di[N-methyl]-carbamoyl-4-[3,4-methoxy]phenyl-1, 4-dihyfropyridine hemihydrate and 2,6-dimethyl-3,5-di[N-methyl]-carbamoyl-4-[furan]-1,4-dihyfropyridine. Z. Kristallogr. 214 (1999) 850-856.
    • (1999) Z. Kristallogr. , vol.214 , pp. 850-856
    • Bidya Sagar, M.1    Ravikumar, K.2    Mehdi, S.3    Sadanandam, Y.S.4
  • 36
    • 0025870869 scopus 로고
    • Dihydropyrimidine calcium channel blockers. 5. Bicyclic dihydropyrimidines as potent mimics of dihydropyridines
    • Atwal, K. S.; Moreland, S.: Dihydropyrimidine calcium channel blockers. 5. Bicyclic dihydropyrimidines as potent mimics of dihydropyridines. Bioorg. Med. Chem. Lett. 1 (1991) 291-294.
    • (1991) Bioorg. Med. Chem. Lett. , vol.1 , pp. 291-294
    • Atwal, K.S.1    Moreland, S.2
  • 37
    • 0034708729 scopus 로고    scopus 로고
    • X-ray structure, conformational analysis. Enantioseparation, and determination of absolute configuration of the Mitotic Kinesin. Eg5 Inhibitor Monastrol
    • Kappe, C. O. Shishkin, O. V.; Uray, G.; Verdino, P.: X-ray structure, conformational analysis, Enantioseparation, and determination of absolute configuration of the Mitotic Kinesin. Eg5 Inhibitor Monastrol. Tetrahedron 56 (2000) 1859-1862.
    • (2000) Tetrahedron , vol.56 , pp. 1859-1862
    • Kappe, C.O.1    Shishkin, O.V.2    Uray, G.3    Verdino, P.4
  • 38
    • 1642455853 scopus 로고    scopus 로고
    • Crystal and molecular structures of 1,4-dihydro-6-methyl-5-N,N-diethylcarbamoyl-4-phenyl-2-(3 H)pyrimidinethione and 1,4-dihydro-6-methyl-5,N-methylcarbamoyl-4-(2′-nitrophenyl)-2(3 H)-pyrimidinethione hemihydrate
    • Accepted
    • Chandra Mohan, K.; Ravikumar, K.; Meera M. Shetty,; Thiyagarajan, S.; Rajan, S. S.: Crystal and molecular structures of 1,4-dihydro-6-methyl-5-N,N-diethylcarbamoyl-4-phenyl-2-(3 H)pyrimidinethione and 1,4-dihydro-6-methyl-5,N-methylcarbamoyl-4-(2′-nitrophenyl)-2(3 H)-pyrimidinethione hemihydrate. J. Chem. Crystallogr. Accepted.
    • J. Chem. Crystallogr.
    • Chandra Mohan, K.1    Ravikumar, K.2    Shetty, M.M.3    Thiyagarajan, S.4    Rajan, S.S.5


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