Synthesis and Theoretical Characterization of Some New 4-Substituted-1,3-diphenyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazoles with Potential Pharmacological Activity

被引：7

作者：

Siwek, Agata ^{[1
]}

Wujec, Monika ^{[1
]}

Dobosz, Maria ^{[1
]}

Paneth, Piotr ^{[2
]}

机构：

[1] Med Univ, Fac Pharm, Dept Organ Chem, PL-20081 Lublin, Poland

[2] Tech Univ Lodz, Inst Appl Radiat Chem, PL-90924 Lodz, Poland

来源：

HETEROATOM CHEMISTRY | 2008年 / 19卷 / 07期

关键词：

D O I：

10.1002/hc.20499

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Synthesis of some new triazoles fused to triazoles 5a-c or thiadiazoles 6a-c and the thiolthione tautomeric equilibrium study of the title compounds are reported. The "rule of five" and complementary criteria of pharmacokinetic properties were determined to predict whether these compounds are orally bioavailable. Semiempirical parameterizations have been critically benchmarked for the thiol-thione tautomeric equilibrium against the DFT calculations. it was shown that unlike the AM1 and PM3 Hamiltonians, which erroneously predict higher stability of the thiol tautomer, the newly developed RM1 Hamiltonian, on the other hand, predicts energetics of this equilibrium in excellent agreement with the DFT results. (C) 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:713-718, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20499

引用

页码：713 / 718

页数：6

共 50 条

[1] Heterocyclic synthesis using nitrile imines 6. Synthesis of some new substituted 4,5-dihydro-1H-1,2,4-triazoles
Dalloul, H. M.
Al-Abadla, N. S.
El-Nwairy, Kh. A.
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2007, (03): : 392 - 397
[2] Heterocyclic synthesis using nitrile imines. 6. Synthesis of some new substituted 4,5-dihydro-1H-1,2,4-triazoles
Dalloul H.M.
Al-Abadla N.S.
El-Nwairy Kh.A.
Chem. Heterocycl. Compd., 2007, 3 (314-319): : 314 - 319
[3] Synthesis of new sulfinyl derivatives of 4,5-diphenyl-4H-1,2,4-triazoles
Rodygin, K. S.
Rubtsova, S. A.
Kuchin, A. V.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 47 (09) : 1433 - 1435
[4] Synthesis of new sulfinyl derivatives of 4,5-diphenyl-4H-1,2,4-triazoles
K. S. Rodygin
S. A. Rubtsova
A. V. Kuchin
Russian Journal of Organic Chemistry, 2011, 47 : 1433 - 1435
[5] Synthesis of some 4,5-dihydro-1H-1,2,4-triazolo-5-ones
Yüksek, H
Bahçeci, S
Ocak, Z
Alkan, M
Ermis, B
Mutlu, T
Ocak, M
Özdemir, M
INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2004, 13 (04) : 369 - 372
[6] SYNTHESIS OF NOVEL DIHYDRO-1,2,4-TRIAZOLES FROM THIOSEMICARBAZONES VIA 1,4-DIACETYL-3-METHYLSULFONYL-4,5-DIHYDRO-1H-1,2,4-TRIAZOLES AS KEY INTERMEDIATES
TOYOOKA, K
KUBOTA, S
CHEMICAL & PHARMACEUTICAL BULLETIN, 1988, 36 (01) : 96 - 106
[7] Synthesis of new 4,5-dihydro-1H-1,2,4-triazol-5-ones
Ikizler, A
Bahceci, S
Ikizler, AA
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1996, 35 (02): : 137 - 140
[8] Reactions of 4-Amino-4,5-dihydro-1H-1,2,4-triazol-5-ones and 4-amino-4H-1,2,4-triazoles with some carboxylic acid anhydrides
Bahceci, S
Ince, N
Ikizler, A
TURKISH JOURNAL OF CHEMISTRY, 1998, 22 (03): : 237 - 241
[9] Synthesis, characterization and theoretical determination of corrosion inhibitor activities of some new 4,5-dihydro-1H-1,2,4-Triazol-5-one derivatives
Beytur, Murat
Irak, Zeynep Turhan
Manap, Sevda
Yuksek, Haydar
HELIYON, 2019, 5 (06)
[10] 1,2,4-TRIAZOLES .5. A FACILE SYNTHESIS OF 1,5-DIPHENYL-3-(SUBSTITUTED OXY)-1H-1,2,4-TRIAZOLES
CZOLLNER, L
SZILAGYI, G
LANGO, J
JANAKY, J
ARCHIV DER PHARMAZIE, 1990, 323 (04) : 221 - 223

← 1 2 3 4 5 →