(6-硝基-2-氧代-1,3-苯并噁唑-3(2H)-基)乙酸 | 19739-41-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 中文名称: (6-硝基-2-氧代-1,3-苯并噁唑-3(2H)-基)乙酸
• 英文名称: 2-(6-nitro-2-oxobenzo[d]oxazol-3(2H)-yl)acetic acid
• 英文别名: (6-nitro-2-oxo-benzooxazol-3-yl)-acetic acid；(6-nitro-2-oxo-1,3-benzoxazol-3(2H)-yl)acetic acid；2-(6-nitro-2-oxo-1,3-benzoxazol-3-yl)acetic acid
• CAS: 19739-41-4
• 化学式: C₉H₆N₂O₆
• mdl: MFCD06386687
• 分子量: 238.156
• InChiKey: IAYXNJKBPWCTMZ-UHFFFAOYSA-N

物化性质

• 沸点：
  474.0±55.0 °C(Predicted)
• 密度：
  1.687±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-噻吩甲胺 、 (6-硝基-2-氧代-1,3-苯并噁唑-3(2H)-基)乙酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以74.7%的产率得到2-(6-nitro-2-oxobenzo[d]oxazol-3(2H)-yl)-N-(thiophen-2-ylmethyl)acetamide
  参考文献：
  名称：

  Development of benzo[d]oxazol-2(3H)-ones derivatives as novel inhibitors of Mycobacterium tuberculosis InhA

  摘要：

  A series of twenty seven substituted 2-(2-oxobenzo[d]oxazol-3(2H)-yl) acetamide derivatives were designed based on our earlier reported Mycobacterium tuberculosis (MTB) enoyl-acyl carrier protein reductase (InhA) lead. Compounds were evaluated for MTB InhA inhibition study, in vitro activity against drug-sensitive and -resistant MTB strains, and cytotoxicity against RAW 264.7 cell line. Among the compounds tested, 2-(6-nitro-2-oxobenzo[d] oxazol-3(2H)-yl)-N-(5-nitrothiazol-2-yl) acetamide (30) was found to be the most promising compound with IC50 of 5.12 +/- 0.44 mu M against MTB InhA, inhibited drug sensitive MTB with MIC 17.11 mu M and was non-cytotoxic at 100 mu M. The interaction with protein and enhancement of protein stability in complex with compound 30 was further confirmed biophysically by differential scanning fluorimetry. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.08.031
• 作为产物：
  描述：

  6-硝基苯并恶唑-2(3H)-酮 在 水 、 sodium hydride 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 5.0h， 生成 (6-硝基-2-氧代-1,3-苯并噁唑-3(2H)-基)乙酸
  参考文献：
  名称：

  Development of benzo[d]oxazol-2(3H)-ones derivatives as novel inhibitors of Mycobacterium tuberculosis InhA

  摘要：

  A series of twenty seven substituted 2-(2-oxobenzo[d]oxazol-3(2H)-yl) acetamide derivatives were designed based on our earlier reported Mycobacterium tuberculosis (MTB) enoyl-acyl carrier protein reductase (InhA) lead. Compounds were evaluated for MTB InhA inhibition study, in vitro activity against drug-sensitive and -resistant MTB strains, and cytotoxicity against RAW 264.7 cell line. Among the compounds tested, 2-(6-nitro-2-oxobenzo[d] oxazol-3(2H)-yl)-N-(5-nitrothiazol-2-yl) acetamide (30) was found to be the most promising compound with IC50 of 5.12 +/- 0.44 mu M against MTB InhA, inhibited drug sensitive MTB with MIC 17.11 mu M and was non-cytotoxic at 100 mu M. The interaction with protein and enhancement of protein stability in complex with compound 30 was further confirmed biophysically by differential scanning fluorimetry. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.08.031

文献信息

• Lespagnol,A. et al., Chimica Therapeutica, 1967, vol. 2, p. 343 - 346
  作者：Lespagnol,A. et al.

  DOI：——

  日期：——
• Development of benzo[d]oxazol-2(3H)-ones derivatives as novel inhibitors of Mycobacterium tuberculosis InhA
  作者：Ganesh S. Pedgaonkar、Jonnalagadda Padma Sridevi、Variam Ullas Jeankumar、Shalini Saxena、Parthiban Brindha Devi、Janupally Renuka、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.bmc.2014.08.031

  日期：2014.11

  A series of twenty seven substituted 2-(2-oxobenzo[d]oxazol-3(2H)-yl) acetamide derivatives were designed based on our earlier reported Mycobacterium tuberculosis (MTB) enoyl-acyl carrier protein reductase (InhA) lead. Compounds were evaluated for MTB InhA inhibition study, in vitro activity against drug-sensitive and -resistant MTB strains, and cytotoxicity against RAW 264.7 cell line. Among the compounds tested, 2-(6-nitro-2-oxobenzo[d] oxazol-3(2H)-yl)-N-(5-nitrothiazol-2-yl) acetamide (30) was found to be the most promising compound with IC50 of 5.12 +/- 0.44 mu M against MTB InhA, inhibited drug sensitive MTB with MIC 17.11 mu M and was non-cytotoxic at 100 mu M. The interaction with protein and enhancement of protein stability in complex with compound 30 was further confirmed biophysically by differential scanning fluorimetry. (C) 2014 Elsevier Ltd. All rights reserved.