tert-butyl 2-(6-chloro-2-oxobenzo[d]oxazol-3(2H)-yl)acetate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl 2-(6-chloro-2-oxobenzo[d]oxazol-3(2H)-yl)acetate
• 英文别名: N-(t-butoxycarbonylmethyl)-6-chloro-2-benzoxazolone；tert-butyl 2-(6-chloro-2-oxo-1,3-benzoxazol-3-yl)acetate
• 化学式: C₁₃H₁₄ClNO₄
• 分子量: 283.711
• InChiKey: ONPQNPOMGRUBOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(6-chloro-2-oxobenzo[d]oxazol-3(2H)-yl)acetate 在 水 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以87.7%的产率得到2-(6-chloro-2-oxobenzo[d]oxazol-3(2H)-yl)acetic acid
  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：

  2-氨基-5-氯苯酚 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 5.0h， 生成 tert-butyl 2-(6-chloro-2-oxobenzo[d]oxazol-3(2H)-yl)acetate
  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

• BCL6 INHIBITORS AS ANTICANCER AGENTS
  申请人：Cornell University

  公开号：US20160166549A1

  公开（公告）日：2016-06-16

  The invention provides compositions and methods for blocking the BCL6 BTB domain with small molecule, non-peptide compounds as disclosed and claimed herein. BCL6 is a transcriptional repressor of the BTB-POZ (brie a brae, tramtrack, broad complex/pox virus zincfinger) family of proteins. It is required for normal development of germinal center (GC) B-cells and is also the most commonly involvedoncogene in diffuse large B-celllymphomas (DLBCLs), and constitutive expression of BCL6 in GC B-cells causes DLBCL in mice.

  本发明提供了一种使用小分子非肽化合物阻断BCL6 BTB结构域的组合物和方法，如本文所述和索要的。BCL6是BTB-POZ（brie a brae，tramtrack，broad complex/pox virus zincfinger）蛋白家族的转录抑制因子。它是生殖中心（GC）B细胞正常发育所必需的，并且也是弥漫性大B细胞淋巴瘤（DLBCLs）中最常涉及的癌基因，GC B细胞中的BCL6的构成表达会导致小鼠DLBCL。
• US9943506B2
  申请人：——

  公开号：US9943506B2

  公开（公告）日：2018-04-17
• 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.