Mechanism of Thiol-Induced Nitrogen(II) Oxide Donation by Furoxans: a Quantum-Chemical Study

被引：11

作者：

Burov, Oleg N. ^{[1
]}

Kletskii, Mikhail E. ^{[1
]}

Fedik, Nikita S. ^{[1
]}

Lisovin, Anton V. ^{[1
]}

Kurbatov, Sergey V. ^{[1
]}

机构：

[1] Southern Fed Univ, 7 Zorge St, Rostov Na Donu 344090, Russia

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2015年 / 51卷 / 11-12期

基金：

俄罗斯科学基金会;

关键词：

furoxans; nitrogen(II) oxide; DFT calculations; thiol-induced NO donation mechanism; NITRIC-OXIDE; VASODILATOR ACTION; S-NITROSOCYSTEINE; OXIDATIVE STRESS; RELAXING FACTOR; PEROXYNITRITE; NITROGLYCERIN; BENZOFUROXAN; METABOLITES; DERIVATIVES;

D O I：

10.1007/s10593-016-1804-z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Quantum-chemical calculations according to DFT with UB3LYP functional in the 6-311++G** basis set, and accounting for solvation effects by the polarized continuum method were used to study the mechanisms of thiol-induced fragmentation of unsubstituted and annulated furoxans with the elimination of nitrogen(II) oxide. A preference for NO formation according to the radical mechanism involving an attack by sulfanyl radical (HSE (TM)) on the carbon atom bonded to the N-oxide group was demonstrated for all systems. Anionic mechanisms involving HS- anions were not feasible in any of the cases due to high endothermic effects.

引用

页码：951 / 960

页数：10

共 68 条

[1] Reactive oxygen species in spermatozoa: methods for monitoring and significance for the origins of genetic disease and infertility [J].

Baker, MA ;

Aitken, RJ .

REPRODUCTIVE BIOLOGY AND ENDOCRINOLOGY, 2005, 3 (1)

[2] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652

[3] DENSITY-FUNCTIONAL EXCHANGE-ENERGY APPROXIMATION WITH CORRECT ASYMPTOTIC-BEHAVIOR [J].

BECKE, AD .

PHYSICAL REVIEW A, 1988, 38 (06) :3098-3100

[4]

Beckman Joseph S., 1995, Methods (Orlando), V7, P35, DOI 10.1006/meth.1995.1005

[5] CARDIOVASCULAR ACTIONS OF THE FUROXAN CAS-1609, A NOVEL NITRIC-OXIDE DONOR [J].

BOHN, H ;

BRENDEL, J ;

MARTORANA, PA ;

SCHONAFINGER, K .

BRITISH JOURNAL OF PHARMACOLOGY, 1995, 114 (08) :1605-1612

[6] Methods to detect nitric oxide and its metabolites in biological samples [J].

Bryan, Nathan S. ;

Grisham, Matthew B. .

FREE RADICAL BIOLOGY AND MEDICINE, 2007, 43 (05) :645-657

[7]

BUTLER AR, 1994, PORTL PR P, V8, P259

[8]

Cerecetto H, 2007, TOP HETEROCYCL CHEM, V10, P265, DOI 10.1007/7081_2007_064

[9] Identification of the enzymatic mechanism of nitroglycerin bioactivation [J].

Chen, ZQ ;

Zhang, J ;

Stamler, JS .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2002, 99 (12) :8306-8311

[10]

Chiou C. C. Y., 1995, J OCUL PHARMACOL TH, V11, P1

← 1 2 3 4 5 6 7 →