2-(2-氧代-1,3-苯并恶唑-3-基)-N-苯基乙酰胺 | 154935-61-2

• 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: 2-(2-氧代-1,3-苯并恶唑-3-基)-N-苯基乙酰胺
• 英文名称: 2-(2-oxobenzo[d]oxazol-3(2H)-yl)-N-phenylacetamide
• 英文别名: 2-(2-oxo-1,3-benzoxazol-3-yl)-N-phenylacetamide
• CAS: 154935-61-2
• 化学式: C₁₅H₁₂N₂O₃
• 分子量: 268.272
• InChiKey: BOEVIAMMZHSRGP-UHFFFAOYSA-N

物化性质

• 密度：
  1.371±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  tert-butyl 2-(2-oxobenzo[d]oxazol-3(2H)-yl)acetate 在 水 、 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 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 2-(2-氧代-1,3-苯并恶唑-3-基)-N-苯基乙酰胺
  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

• Synthesis of Some 2(3H)-Benzoxazolone Derivatives and theirin-vitro Effects on Human Leukocyte Myeloperoxidase Activity
  作者：Zeynep Soyer、Meral Bas、Aysun Pabuccuoglu、Varol Pabuccuoglu

  DOI：10.1002/ardp.200500106

  日期：2005.9

  disorders. In this study, twenty ω‐[2‐oxo‐3H‐benzoxazol‐3‐yl]‐N‐phenylacetamide and propionamide derivatives having substituents of different lipophilic and electronic nature on the N‐phenyl ring were synthesized to evaluate the inhibitory effects on in vitro leukocyte MPO chlorinating activity. The most active compounds in the series were the derivatives bearing 2‐methyl and 4‐nitro substituent on

  髓过氧化物酶 (MPO) 是一种由多形核白细胞表达的血红素蛋白，可产生强氧化剂，在炎症和某些发病机制（如神经退行性疾病）过程中会导致组织损伤。本研究合成了20个ω-[2-氧代-3H-苯并恶唑-3-基]-N-苯乙酰胺和丙酰胺衍生物，在N-苯环上具有不同亲油性和电子性质的取代基，以评估对in的抑制作用。体外白细胞 MPO 氯化活性。该系列中最活跃的化合物是在 N-苯环上带有 2-甲基和 4-硝基取代基的衍生物。
• 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.