2-<acetamido>benzoic acid | 140934-46-9

• 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-<acetamido>benzoic acid
• 英文别名: 2-{[N-(4-Methoxyphenyl)glycyl]amino}benzoic acid；2-[[2-(4-methoxyanilino)acetyl]amino]benzoic acid
• CAS: 140934-46-9
• 化学式: C₁₆H₁₆N₂O₄
• 分子量: 300.314
• InChiKey: KFSLWYUFYFKGRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-<acetamido>benzoic acid 在 氯化亚砜 、 PPA 、 Polyphosphoric acid (PPA) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 11-chloro-7-methoxy-10H-indolo<3,2-b>quinoline
  参考文献：
  名称：

  稠合喹啉衍生物的合成及其抗肿瘤活性。二。新颖的4-和7-羟基吲哚并[3,2-b]喹啉。

  摘要：

  制备了新的吲哚并[3,2-b]喹啉衍生物（1c-f），其在前导化合物1a的4位或7位带有甲氧基或羟基，并在小鼠中具有抗P388的抗肿瘤活性。被检查。除4-羟基衍生物（1d）外，它们均显示出显着的活性。在这些化合物中，7-羟基衍生物（1f）是最有效的化合物（最佳剂量= 50 mg / kg，治疗组/对照组的中位生存时间（T / C）大于330％，治愈= 5 / 6）。

  DOI：

  10.1248/cpb.40.528
• 作为产物：
  描述：

  邻氨基苯甲酸 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-<acetamido>benzoic acid
  参考文献：
  名称：

  Bis-alkylamine Indolo[3,2-b]quinolines as Hemozoin Ligands: Implications for Antimalarial Cytostatic and Cytocidal Activities

  摘要：

  To get insight into the relevance of targeting hemozoin (Hz) crystals, two isomeric series, N5,N10-bis-alkylamine (2a-k) and N10,O11-bis-alkylamine (3a-k) indolo[3,2-b]quinolines, were evaluated for their in vitro activity against chloroquine (CQ)-resistant and sensitive strains of Plasmodium falciparum. In general, compounds of series 3 were more active than isomers 2, with IC50/LD50 ranging from 25/233 nM (3i) to 1.3 (3a)/10.7 (3b) mu M. SAR analyses showed that lipophilicity and chlorine substitution at C3 increased both cytostatic and cytocidal activities. Both series bound to hematin monomer, inhibited beta-hematin formation in vitro, delayed intraerythrocytic parasite development with apparent inhibition of Hz biocrystallization, and showed higher cytocidal activity against schizonts. In addition, cytostatic and cytocidal activities of series 3, but not those of isomers 2, correlated with calculated vacuole accumulation ratios, suggesting different capacities of 2 and 3 to bind to the Hz crystal face {001} exposed on the vacuole aqueous medium and different mechanisms of cytocidal potency.

  DOI：

  10.1021/jm500075d

文献信息

• Cryptolepine analogs with hypoglycemic activity
  申请人：Shaman Pharmaceuticals, Inc.

  公开号：US05681958A1

  公开（公告）日：1997-10-28

  Novel cryptolepine analogs useful as hypoglycemic agents and methods for their use as hypoglycemic agents, for example, in the treatment of diabetes, and a method for their synthesis are described. As hypoglycemic agents, the novel crytolepine analogs are useful for the treatment of insulin-dependent diabetes mellitus (IDDM or Type I) and non-insulin dependent diabetes mellitus (NIDDM or Type II).

  本发明涉及一种新型的类似加密藤碱的化合物，其作为降血糖剂具有应用价值，并且提供了这些化合物用于治疗糖尿病的方法，以及它们的合成方法。作为降血糖剂，这些新型的类似加密藤碱的化合物对胰岛素依赖性糖尿病（IDDM或1型）和非胰岛素依赖性糖尿病（NIDDM或2型）的治疗具有应用价值。
• Bis-alkylamine Indolo[3,2-<i>b</i>]quinolines as Hemozoin Ligands: Implications for Antimalarial Cytostatic and Cytocidal Activities
  作者：Alexandra Paulo、Marta Figueiras、Marta Machado、Catarina Charneira、João Lavrado、Sofia A. Santos、Dinora Lopes、Jiri Gut、Philip J. Rosenthal、Fátima Nogueira、Rui Moreira

  DOI：10.1021/jm500075d

  日期：2014.4.24

  To get insight into the relevance of targeting hemozoin (Hz) crystals, two isomeric series, N5,N10-bis-alkylamine (2a-k) and N10,O11-bis-alkylamine (3a-k) indolo[3,2-b]quinolines, were evaluated for their in vitro activity against chloroquine (CQ)-resistant and sensitive strains of Plasmodium falciparum. In general, compounds of series 3 were more active than isomers 2, with IC50/LD50 ranging from 25/233 nM (3i) to 1.3 (3a)/10.7 (3b) mu M. SAR analyses showed that lipophilicity and chlorine substitution at C3 increased both cytostatic and cytocidal activities. Both series bound to hematin monomer, inhibited beta-hematin formation in vitro, delayed intraerythrocytic parasite development with apparent inhibition of Hz biocrystallization, and showed higher cytocidal activity against schizonts. In addition, cytostatic and cytocidal activities of series 3, but not those of isomers 2, correlated with calculated vacuole accumulation ratios, suggesting different capacities of 2 and 3 to bind to the Hz crystal face 001} exposed on the vacuole aqueous medium and different mechanisms of cytocidal potency.
• Chang, Ming-rong; Takeuchi, Yasuo; Hashigaki, Kuniko, Heterocycles, 1992, vol. 33, # 1, p. 147 - 152
  作者：Chang, Ming-rong、Takeuchi, Yasuo、Hashigaki, Kuniko、Yamato, Masatoshi

  DOI：——

  日期：——
• US5741926A
  申请人：——

  公开号：US5741926A

  公开（公告）日：1998-04-21
• [EN] CRYPTOLEPINE ANALOGS WITH HYPOGLYCEMIC ACTIVITY<br/>[FR] ANALOGUES DE CRYPTOLEPINE A ACTIVITE HYPOGLYCEMIQUE
  申请人：SHAMAN PHARMACEUTICALS, INC.

  公开号：WO1996010015A1

  公开（公告）日：1996-04-04

  (EN) Novel cryptolepine analogs useful as hypoglycemic agents and methods for their use as hypoglycemic agents, for example, in the treatment of diabetes, and a method for their synthesis are described. As hypoglycemic agents, the novel cryptolepine analogs are useful for the treatment of insulin-dependent diabetes mellitus (IDDM or Type I) and non-insulin dependent diabetes mellitus (NIDDM or Type II).(FR) Nouveaux analogues de cryptolépine utiles comme agents hypoglycémiques, méthodes d'utilisation de ces analogues comme agents hypoglycémiques, par exemple, pour le traitement du diabète, et méthodes de synthèse de ces analogues. En tant qu'agents hypoglycémiques, ces nouveaux analogues de cryptolépine se révèlent utiles pour le traitement du diabète sucré insulino-dépendant (IDDM ou Type I) et du diabète sucré non insulino-dépendant (NIDDM OU Type II).