2-hydroxymethyl-4,6-dimethylisothiazolo[5,4-b]pyridin-3(2H)-one | 205171-26-2

• 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-hydroxymethyl-4,6-dimethylisothiazolo[5,4-b]pyridin-3(2H)-one
• 英文别名: 2-(Hydroxymethyl)-4,6-dimethyl-isothiazolo[5,4-b]pyridin-3-one；2-(hydroxymethyl)-4,6-dimethyl-[1,2]thiazolo[5,4-b]pyridin-3-one
• CAS: 205171-26-2
• 化学式: C₉H₁₀N₂O₂S
• 分子量: 210.257
• InChiKey: DZZPVUVTGSGLPL-UHFFFAOYSA-N

物化性质

• 沸点：
  425.0±55.0 °C(Predicted)
• 密度：
  1.402±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  78.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydroxymethyl-4,6-dimethylisothiazolo[5,4-b]pyridin-3(2H)-one 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 0.25h， 生成 4,6-二甲基异噻唑并[5,4-b]吡啶-3(2H)-酮
  参考文献：
  名称：

  Malinka; Rutkowska, Il Farmaco, 1997, vol. 52, # 10, p. 595 - 601

  摘要：

  DOI：
• 作为产物：
  描述：

  聚合甲醛 、 4,6-二甲基异噻唑并[5,4-b]吡啶-3(2H)-酮 以 乙醇 为溶剂， 反应 0.25h， 生成 2-hydroxymethyl-4,6-dimethylisothiazolo[5,4-b]pyridin-3(2H)-one
  参考文献：
  名称：

  Malinka, Habil W.; Sieklucka-Dziuba; Rajtar, Pharmazie, 2000, vol. 55, # 6, p. 416 - 425

  摘要：

  DOI：

文献信息

• Pyrido- and benzisothiazolones as inhibitors of histone acetyltransferases (HATs)
  作者：S. D. Furdas、I. Hoffmann、D. Robaa、B. Herquel、W. Malinka、P. Świątek、A. Akhtar、W. Sippl、M. Jung

  DOI：10.1039/c4md00245h

  日期：——

  We present structure–activity studies on pyrido- and benzisothiazolones as histone acetyltransferase (HAT) inhibitors. Distinct subtype-selectivity profiles were obtained in vitro that correlate with cytotoxicity profiles on cancer cells.

  我们展示了对吡啶并和苯并异噻唑酮作为组蛋白乙酰转移酶（HAT）抑制剂的构效研究。在体外获得了不同的亚型选择性谱，这些谱与对癌细胞的细胞毒性谱相关。
• Malinka, Habil W.; Sieklucka-Dziuba; Rajtar, Pharmazie, 2000, vol. 55, # 6, p. 416 - 425
  作者：Malinka, Habil W.、Sieklucka-Dziuba、Rajtar、Zgodzinski、Kleinrok

  DOI：——

  日期：——
• Synthesis of novel isothiazolopyridines and their in vitro evaluation against Mycobacterium and Propionibacterium acnes
  作者：Wiesław Malinka、Piotr Świątek、Małgorzata Śliwińska、Bogumiła Szponar、Andrzej Gamian、Zbigniew Karczmarzyk、Andrzej Fruziński

  DOI：10.1016/j.bmc.2013.06.027

  日期：2013.9

  In this paper we describe synthesis, structures and some physicochemical properties of 20 isothiazolopyridines 8-13 substituted differently into an isothiazole ring as well as their in vitro antibacterial assays against Mycobacterium tuberculosis H37Rv, Mycobacterium fortuitum PCM 672 and Propionibacterium acnes PCM 2400. Compound 13a was found to be the most active derivative against M. tuberculosis H37Rv, demonstrating 100% growth inhibition of microorganisms in the primary screen (minimum inhibitory concentration [MIC] 6.25 mu g/mL). Nineteen of the prepared compounds were evaluated against M. fortuitum PCM 672 and P. acnes PCM 2400 and only compounds 9 and 12d exhibited excellent activity against individual strains of microorganisms with MIC90 <1 mu g/mL. The inhibitory action of the remaining isothiazolopyridines towards the tested strains of the microorganism was low, absent, or a non-linear correlation prohibited accurate determination of MIC values. Unexpectedly, seven of the remaining isothiazolopyridines tested against M. fortuitum and P. acnes stimulated growth of the microorganisms in the range 10-50% or even more (10b) under experimental conditions. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.
• Synthesis and in vivo pharmacology of new derivatives of isothiazolo[5,4-b]pyridine of Mannich base type
  作者：Wiesław Malinka、Zbigniew Karczmarzyk、Maria Sieklucka-Dziuba、Mirosław Sadowski、Zdzisław Kleinrok

  DOI：10.1016/s0014-827x(01)01157-0

  日期：2001.12

  Recently we reported on 2H-4,6-dimethyl-2-[(4-phenylpiperazin-1-yl)methyl]-3-oxo-2,3-dihydroisothiazolo[5,4-b]pyridine (V), which exhibited high anorectic action in animal models as a result of stimulation of serotoninergic system. This paper describes the synthesis of the series 3-5 of analogues of V prepared from 2-hydroxymethyl-4,6-dimethylisothiazolopyridine (2) and corresponding 4-substituted-piperazines(piperidines) or tetrahydroisoquinoline. The 12 compounds obtained were screened in standard CNS tests in in vivo (mice and rats). In contrast to V, none of its analogues showed serotoninergic activity, whereas several of these compounds were found to be active as weak to moderate analgesic agents. According to X-ray and molecular modeling studies the different pharmacological profile of V and its o-OCH, analog 3a, taken as an example, should be referred back to the conformational restriction incorporated by the o-substitution rather than effects of different lipophlicity or basicity of these compounds. (C) 2001 Elsevier Science S.A. All rights reserved.
• US3965107A
  申请人：——

  公开号：US3965107A

  公开（公告）日：1976-06-22