N-chloroacetyl-5-bromoanthranilic acid | 155104-20-4

• 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: N-chloroacetyl-5-bromoanthranilic acid
• 英文别名: 5-Bromo-2-(2-chloroacetamido)benzoicacid；5-bromo-2-[(2-chloroacetyl)amino]benzoic acid
• CAS: 155104-20-4
• 化学式: C₉H₇BrClNO₃
• 分子量: 292.516
• InChiKey: OFYMACOYOUBHNZ-UHFFFAOYSA-N

物化性质

• 熔点：
  185 °C(Solv: ethanol (64-17-5))
• 沸点：
  486.2±45.0 °C(Predicted)
• 密度：
  1.798±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-chloroacetyl-5-bromoanthranilic acid 在 乙酸酐 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 6-Bromo-2-chloromethyl-3-(4-hydroxy-phenyl)-3H-quinazolin-4-one
  参考文献：
  名称：

  Amin, M. A.; Osman, A. N.; Aziza, M. A., Egyptian Journal of Chemistry, 1995, vol. 38, # 1, p. 113 - 123

  摘要：

  DOI：
• 作为产物：
  描述：

  2-chloroacetamidobenzoic acid 在 溴 作用下， 以 水 为溶剂， 反应 1.0h， 以88%的产率得到N-chloroacetyl-5-bromoanthranilic acid
  参考文献：
  名称：

  Abdel-Alim, M Abdel-Alim; El-Shorbagi, Abdel-Nasser A; El-Shareif, Hosny A H, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, p. 260 - 265

  摘要：

  DOI：

文献信息

• 一种2（3）-对甲硫基苯乙烯基苯并呋喃喹啉衍 生物及其制备方法和应用
  申请人：中山大学

  公开号：CN108530453B

  公开（公告）日：2021-05-11

  本发明涉及一种2（3）‑对甲硫基苯乙烯基苯并呋喃喹啉衍生物及其制备方法和应用。所述衍生物的结构式如式（Ⅰ）或式（Ⅱ）所示：其中，R为C2~3烷二胺基、N‑甲基取代C2~3烷二胺基、4‑N取代哌嗪基、末端取代C1~3烷胺基或吗啉基；X为O或N。在吲哚并喹啉，苯并呋喃喹啉，5‑N‑甲基化吲哚并喹啉，以及5‑N‑甲基化苯并呋喃喹啉化合物母体骨架化合物母体骨架的A环上引入对甲硫基苯乙烯，再在11位上引入不同的胺基侧链，可与NRAS RNA G‑四链体相互作用，具有较好的选择性和活性，且毒性小，抗肿瘤效果好。
• 作为CDK2/Topo I抑制剂的白叶藤碱衍生物及其制备方法和抗肿瘤的应用
  申请人：中国人民解放军北部战区总医院

  公开号：CN115160310B

  公开（公告）日：2023-06-23

  本发明提出一种作为CDK2/Topo I抑制剂的白叶藤碱衍生物及其制备方法和抗肿瘤的应用，本发明合成方法简单，温和；部分衍生物能够同时抑制CDK2和Topo I；3、衍生物的抗肿瘤细胞增值活性显著增强。本发明化合物作为先导化合物在肿瘤治疗中具有重要作用。
• Design, synthesis and biological evaluation of 2-mercapto-3-phenethylquinazoline bearing anilide fragments as potential antitumor agents: Molecular docking study
  作者：Ibrahim A. Al-Suwaidan、Amer M. Alanazi、Alaa A.-M. Abdel-Aziz、Menshawy A. Mohamed、Adel S. El-Azab

  DOI：10.1016/j.bmcl.2013.04.056

  日期：2013.7

  A novel series of 2-(3-phenethyl-4(3H)quinazolin-2-ylthio)-N-substituted anilide and substituted phenyl 2-(3-phenethyl-4(3H) quinazolin-2-ylthio) acetate were designed, synthesized and evaluated for their in-vitro antitumor activity. Compound 15 possessed remarkable broad-spectrum antitumor activity which almost sevenfold more active than the known drug 5-FU with GI(50) values of 3.16 and 22.60 mu M, respectively. Compound 15 exhibited remarkable growth inhibitory activity pattern against renal cancer (GI(50) = 1.77 mu M), colon cancer (GI(50) = 2.02 mu M), non-small cell lung cancer (GI(50) = 2.04 mu M), breast cancer (GI(50) = 2.77 mu M), ovarian cancer (GI(50) = 2.55 mu M) and melanoma cancer (GI(50) = 3.30 mu M). Docking study was performed for compound 15 into ATP binding site of EGFR-TK which showed similar binding mode to erlotinib. (c) 2013 Elsevier Ltd. All rights reserved.
• Akila; Majo; Balasubramanian, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 3, p. 647 - 649
  作者：Akila、Majo、Balasubramanian

  DOI：——

  日期：——
• Synthesis of 3-[4′-(p-chlorophenyl)-thiazol-2′-yl]-2-[(substituted azetidinone/thiazolidinone)-aminomethyl]-6-bromoquinazolin-4-ones as anti-inflammatory agent
  作者：Ashok Kumar、Chatrasal Singh Rajput、Sudhir Kumar Bhati

  DOI：10.1016/j.bmc.2007.01.042

  日期：2007.4

  N-Chloroacetyl-5-bromoanthranilic acid (1), 3-[4'-(p-chlorophenyl)-thiazol-2'-yl]-2-chloromethyl-6-bromoquinazolin-4-one (2), 3-[4'-(p-chlorophenyl)-thiazol-2'-yl]-2-hydrazinomethyl-6-bromoquinazolin-4-one (3), 3-[4'-(p-chlorophenyl)-thiazol-2'-yl]-2- substituted benzylidene aminomethyl-6-bromoquinazolin-4-ones (4-11), 2-[(4'-oxo-3'-chloro-2'-phenylazetidin-l'-yl)aminomethyl]-3 -[4"-(p-chlorophenyl)thiazo1-2"-yl]-6-bromoquinazolin-4-ones (12-19) and 2-(4'-oxo-2'-phenyl-thiazolidin-3'-yl-aminomethyl)3-[4"-(p-chlorophenyl)-thiazol-2"-yl]-6-bromoquinazolin-4-ones (20-27) have been synthesized. All the compounds have been screened for their anti-inflammatory and analgesic activities at the dose of 50 mg/kg po. Compound 21 showed maximum anti-inflammatory (38.35%) and analgesic (37.36%) activities. Compound 21 was also tested for ulcerogenic activity and the UD50 value was found to be 195.6 mg/kg po. The structure of all compounds has been evaluated by elemental analysis (C, H, N) and spectral analysis (IR, H-1 NMR and mass spectrometry). (c) 2007 Published by Elsevier.