2-chloro-N-(4-methyl-3-nitrophenyl)acetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-chloro-N-(4-methyl-3-nitrophenyl)acetamide
• 英文别名: chloro-acetic acid-(4-methyl-3-nitro-anilide)；Chlor-essigsaeure-(4-methyl-3-nitro-anilid)；2-Nitro-4-chloracetamino-toluol
• 化学式: C₉H₉ClN₂O₃
• mdl: MFCD00454957
• 分子量: 228.635
• InChiKey: VIFSOJSNZWHKLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-N-(4-methyl-3-nitrophenyl)acetamide 在 吡啶 、 铁粉 、 氯化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 乙醇 、 水 、 正丁醇 为溶剂， 反应 11.0h， 生成 4-(dimethylamino)-N-(2-methyl-5-{2-[(4-oxo-4H-chromen-7-yl)oxy]acetamido}phenyl)benzamide
  参考文献：
  名称：

  Discovery of 4H-Chromen-4-one Derivatives as a New Class of Selective Rho Kinase (ROCK) Inhibitors, which Showed Potent Activity in ex Vivo Diabetic Retinopathy Models

  摘要：

  Diabetic retinopathy (DR) is a major cause of blindness, and there is a lack of effective treatment at present. Rho-associated coiled-coil containing serine/threonine protein kinases (ROCKs) have recently been suggested as potential targets for the DR treatment. We herein report the discovery of 4H-chromen-4-one derivatives as a new class of ROCK inhibitors. Structure-activity relationship analyses led to the identification of the most active compound, 4-(dimethylamino)-N-(3-{2-[(4-oxo-4H-chromen-7-yl)oxy]acetamido}phenyl) (12j). This compound showed excellent kinase selectivity for ROCK I and ROCK II against 387 other kinases. In retinal explants, compound 12j protected retinal neurons from high glucose-induced oxidative stress and apoptosis-mediated cell death. Furthermore, 12j administration suppressed the improper proliferation of Muller cells and promoted the regression of vascular vessels in retinal explants cultured in a high glucose microenvironment. Collectively, our data suggest that 12j could be a potential lead compound for the treatment of DR, hence deserving further in-depth studies.

  DOI：

  10.1021/acs.jmedchem.9b01143
• 作为产物：
  描述：

  氯乙酰氯 、 4-甲基-3-硝基苯胺 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到2-chloro-N-(4-methyl-3-nitrophenyl)acetamide
  参考文献：
  名称：

  [EN] 2- [ (2-{PHENYLAMINO}-1H-PYRROLO [2, 3-D] PYRIMIDIN-4-YL) AMINO] BENZAMIDE DERIVATIVES AS IGF-1R INHIBITORS FOR THE TREATMENT OF CANCER
  [FR] DÉRIVÉS DE 2-[(2-{PHÉNYLAMINO}-1H-PYRROLO[2,3-D]PYRIMIDIN-4-YL)AMINO]BENZAMIDE EN TANT QU'INHIBITEUR D'IGF-1R POUR LE TRAITEMENT DU CANCER

  摘要：

  新型吡咯吡嘧啶如公式(I)所示，及其药用可接受的衍生物。这些化合物在抑制IGF-1R方面是有用的。

  公开号：

  WO2009020990A1

文献信息

• 2-[2--1H-Pyrrolo[2,3-D]Pyrimidin-4-YL)Amino] Benzamide Derivatives As IGF-1R Inhibitors For The Treatment Of Cancer
  申请人：Chamberlain Stanley Dawes

  公开号：US20100204196A1

  公开（公告）日：2010-08-12

  Novel pyrrolopyrimidines as shown in formula (I): and pharmaceutically acceptable derivatives thereof. The compounds are useful in the inhibition of IGF-1R.

  式(I)所示的新型吡咯吡咪啉及其药学上可接受的衍生物。这些化合物在抑制IGF-1R方面是有用的。
• 2-[2-{phenylamino}-1H-pyrrolo[2,3-D]pyrimidin-4-yl)amino] benzamide derivatives as IGF-1R inhibitors for the treatment of cancer
  申请人：GlaxoSmithKline LLC

  公开号：US07981903B2

  公开（公告）日：2011-07-19

  Novel pyrrolopyrimidines as shown in formula (I): and pharmaceutically acceptable derivatives thereof. The compounds are useful in the inhibition of IGF-1R.

  式(I)所示的新型吡咯吡嗪化合物及其药学上可接受的衍生物。这些化合物可用于抑制IGF-1R。
• Beckurts; Frerichs, Archiv der Pharmazie, 1915, vol. 253, p. 246
  作者：Beckurts、Frerichs

  DOI：——

  日期：——
• 2- [ (2-{PHENYLAMINO}-1H-PYRROLO [2, 3-D]PYRIMIDIN-4-YL) AMINO]BENZAMIDE DERIVATIVES AS IGF-1R INHIBITORS FOR THE TREATMENT OF CANCER
  申请人：GlaxoSmithKline Intellectual Property Development Limited

  公开号：EP2188292B1

  公开（公告）日：2013-05-29
• US7981903B2
  申请人：——

  公开号：US7981903B2

  公开（公告）日：2011-07-19