2-hexylisothiazolo<5,4-b>pyridin-3(2H)-one | 154344-44-2

• 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: 2-hexylisothiazolo<5,4-b>pyridin-3(2H)-one
• 英文别名: 2-Hexylisothiazolo[5,4-b]pyridin-3-one；2-hexyl-[1,2]thiazolo[5,4-b]pyridin-3-one
• CAS: 154344-44-2
• 化学式: C₁₂H₁₆N₂OS
• 分子量: 236.338
• InChiKey: KMMATJGETOAJKC-UHFFFAOYSA-N

物化性质

• 沸点：
  381.8±34.0 °C(predicted)
• 密度：
  1.167±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hexylisothiazolo<5,4-b>pyridin-3(2H)-one 在 劳森试剂 、 硫化氢 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 0.5h， 生成 1,2-dithiolo<5,4-b>pyridin-3-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 劳森试剂 、 mercury(II) diacetate 、 碘 、 碳酸氢钠 、 sulfur 、 溶剂黄146 作用下， 以 乙醇 、 氯仿 、 甲苯 为溶剂， 反应 5.5h， 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

文献信息

• 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.