3H-[1,2]-dithiolo[3,4-b]pyridine-3-thione | 3445-78-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3H-[1,2]-dithiolo[3,4-b]pyridine-3-thione
• 英文别名: 3H-[1,2]dithiolo[3,4-b]pyridine-3-thione；dithiolo[3,4-b]pyridine-3-thione
• CAS: 3445-78-1
• 化学式: C₆H₃NS₃
• mdl: MFCD12028174
• 分子量: 185.295
• InChiKey: MQBHSIJPOQETLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3H-[1,2]-dithiolo[3,4-b]pyridine-3-thione 在 mercury(II) diacetate 、 碘 、 碳酸氢钠 、 溶剂黄146 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 0.5h， 生成 2-hexylisothiazolo<5,4-b>pyridin-3(2H)-one
  参考文献：
  名称：

  3H-[1,2]Dithiolo[3,4-b]pyridine-3-thione and its derivatives Synthesis and antimicrobial activity

  摘要：

  A series of 2-substituted isothiazolo[5,4-b]pyridine-3(2H)-thiones isothiazolo[5,4-b]pyridin-3(2H)-ones, N-substituted 2-sulfanylnicotinamides and the corresponding carbothioamide derivatives were synthesized and evaluated for their antimicrobial activity against several strains of Gram + and Gram - bacteria and fungi. Chemical syntheses were resumed into a comprehensive cyclic route that enables the reversible conversion for each derivative of the series considered. Among the tested compounds the N-(aralkyl)-2-sulfanylnicotinamides show the highest fungitoxicity (MIC = 1.25-5 mug/ml). The best activity towards Gram-positive bacteria was in the range of 2.5-5 mug/ml. Activity against Gram-negative bacteria was generally very poor for all compounds. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(00)00084-7
• 作为产物：
  描述：

  2-巯基烟酸 在 tetraphosphorus decasulfide 作用下， 以 吡啶 为溶剂， 反应 2.0h， 以37%的产率得到3H-[1,2]-dithiolo[3,4-b]pyridine-3-thione
  参考文献：
  名称：

  Baggaley, Keith H.; Jennings, L. John A.; Tyrrell, A. William R., Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1393 - 1396

  摘要：

  DOI：

文献信息

• Synthesis of 6,7-Dihydropyrrolo[2,1-<i>c</i> ][1,3]thiazino[3,2-<i>a</i> ]pyrazine-4(11b<i>H</i> )-(thi)ones from 1,2-Dithiolo-3-(thi)ones
  作者：Vladimir A. Ogurtsov、Yury V. Karpychev、Yulia V. Nelyubina、Petr V. Primakov、Panayiotis A. Koutentis、Oleg A. Rakitin

  DOI：10.1002/ejoc.201900142

  日期：2019.7.14

  Both monocyclic and fused 1,2‐di‐thiolo‐3‐(thi)ones underwent addition of 3,4‐dihydropyrrolo[1,2‐a]pyrazine with selective extrusion of S2 atom and formation of 6,7‐dihydropyrrolo[2,1‐c][1,3]thi‐azino[3,2‐a]pyrazine‐4(11bH)‐(thi)ones. 1,2‐Dithiolo‐3‐one moiety was found more reactive than the corresponding 1,2‐dithiole‐3‐thione one.

  单环和稠合的1,2-二硫代3-（thi）酮都加入了3,4-二氢吡咯并[1,2- a ]吡嗪，并选择性挤出了S2原子并形成了6,7-二氢吡咯并[2] ，1‐ c ] [1,3]噻嗪[3,2‐ a ]吡嗪‐4（11b H）‐（噻吩）酮。发现1,2-二硫代-3-酮比相应的1,2-二硫代-3-硫酮具有更高的反应活性。
• Synthesis of 1-[(1,2-dithiol-3-ylidene)methyl]pyrrolo[1,2-a]pyrazines and 2-[(1,2-dithiol-3-ylidene)methyl]pyridines from 1,2-dithiole-3-thiones
  作者：V. A. Ogurtsov、Yu. V. Karpychev、O. A. Rakitin

  DOI：10.1007/s11172-013-0144-8

  日期：2013.4

  Benzo- and pyridoannulated 1,2-dithiole-3-thiones react with compounds containing an activated methyl group such as 1-methyl-3,4-dihydropyrrolo[1,2-a]pyrazine and 2-methylpyridines to furnish substituted 1,2-dithiol-3-ylidenes.

  苯并和吡啶稠合的1,2-二硫杂环戊烯-3-硫酮与含有活性甲基的化合物，如1-甲基-3,4-二氢吡咯并[1,2-a]吡嗪和2-甲基吡啶反应，生成取代的1,2-二硫醇-3-亚基。
• On the reaction between 3<i>H</i>-1,2-dithiolo[3,4-<i>b</i>]pyridine-3-thione and primary alkyl and arylalkylamines
  作者：Pietro Borgna、Massimo Pregnolato、Anna Gamba Invernizzi、Giorgio Mellerio

  DOI：10.1002/jhet.5570300441

  日期：1993.7

  3H-1,2-Dithiolo[3,4-b]pyridine-3-thione (10) reacts with primary alkylamines to give 1,2-dihydro-2-thioxo-3-pyridinecarbothioamides 11a-g and two minor products. Isothiazolo[5,4-b]pyridine-3(2H)-thiones 12a-g and 3-imino-3H-1,2-dithiolo[3,4-b]pyridines 13a-g were isolated and characterized. Further investigations allowed the synthesis of 12 and 13 in good yield.

  3 H -1,2-二硫代[3,4- b ]吡啶-3-硫酮（10）与伯烷基胺反应，得到1,2-二氢-2-硫代-3-吡啶吡啶碳硫酰胺11a-g和两种次要产物。分离并表征了异噻唑并[5,4 - b ]吡啶-3（2 H）-硫酮12a-g和3-亚氨基-3 H -1,2-二硫代[3,4- b ]吡啶13a-g。进一步的研究允许以高产率合成12和13。
• Synthesis and in Vitro Anti<i>-Mycobacterium </i>Activity of <i>N</i>-Alkyl-1,2-dihydro-2-thioxo-3-pyridinecarbothioamides. Preliminary Toxicity and Pharmacokinetic Evaluation
  作者：Giuseppe Pagani、Massimo Pregnolato、Daniela Ubiali、Marco Terreni、Claudio Piersimoni、Francesco Scaglione、Franco Fraschini、Alicia Rodríguez Gascón、José Luis Pedraz Muñoz

  DOI：10.1021/jm991044p

  日期：2000.1.1

  Disseminated infections with Mycobacterium tuberculosis (MT) and Mycobacterium avium complex (MAC) are increasingly opportunistic diseases in patients with advanced acquired human immunodeficiency syndrome (AIDS). A series of N-alkyl-1,2-dihydro-2-thioxo-3-pyridinecarbothioamides has been synthesized, and MICs for MT and MAC strains, either standard or isolated from infected patients, have been determined. Preliminary tests show a good activity and a very low toxicity for some derivatives. Pharmacokinetic studies in the rat show a very rapid elimination from the body after intravenous administration and a poor absorption after oral administration.
• 1,2-Dithiolan-3-ones and derivatives structurally related to leinamycin. Synthesis and biological evaluation
  作者：Raul Salvetti、Giovanni Martinetti、Daniela Ubiali、Massimo Pregnolato、Giuseppe Pagani

  DOI：10.1016/s0014-827x(03)00134-4

  日期：2003.9

  Leinamycin, an antitumor antibiotic isolated from Streptomyces sp., shows a 1,2-dithiolan-3-one 1-oxide heterocycle that appears to be involved in the biological activity. Several derivatives related to 1,2-dithiolan-3-one 1-oxide have been prepared and their activity as antineoplastic agents have been investigated. The synthesized compounds did not display a significative antitumor or cytotoxic activity in vitro.