2-[[2-(4-甲基苯胺基)乙酰基]氨基]苯甲酸 | 131058-39-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[[2-(4-甲基苯胺基)乙酰基]氨基]苯甲酸
• 英文名称: 2-[2-(p-tolylamino)acetamido]benzoic acid
• 英文别名: N-[(4-methylphenylamino)acetyl]anthranilic acid；Benzoic acid, 2-[[[(4-methylphenyl)amino]acetyl]amino]-；2-[[2-(4-methylanilino)acetyl]amino]benzoic acid
• CAS: 131058-39-4
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: UUHURYUUEJPHIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[[2-(4-甲基苯胺基)乙酰基]氨基]苯甲酸 在 PPA 、 三氯氧磷 作用下， 反应 3.0h， 生成 11-chloro-7-methyl-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。V.甲基吲哚并[3，2-b]喹啉。

  摘要：

  合成了在每个可能位置具有甲基的吲哚并[3,2-b]喹啉衍生物（1b-i）。1-甲基（1b）和9-甲基（1i）衍生物没有活性，但是3-甲基（1d），4-甲基（1e）和6甲基（1f）衍生物表现出较高的处理/控制（T / C）小鼠抗白血病P388的价值和治愈率。这些结果表明，吲哚[3,2-b]喹啉衍生物在3、4和6位的修饰可能是优化前导的有用方法。

  DOI：

  10.1248/cpb.45.2096
• 作为产物：
  描述：

  邻氨基苯甲酸 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 0.17h， 生成 2-[[2-(4-甲基苯胺基)乙酰基]氨基]苯甲酸
  参考文献：
  名称：

  Structure–activity relationship of indoloquinoline analogs anti-MRSA

  摘要：

  Indolo[3,2-b]quinoline analogs (3a-3s), 4-(acridin-9-ylamino) phenol hydrochloride (4), benzofuro[3,2-b]quinoline (3t), indeno[1,2-b] quinolines (3u and 3v) have been synthesized. Those compounds were found to exhibit anti-bacterial activity towards Methicillin-resistant Staphylococcus aureus (anti-MRSA activity). Structure-activity relationship studies were conducted that indoloquinoline ring, benzofuro-quinoline ring and 4-aminophenol group are essential structure for anti-MRSA activity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.10.058

文献信息

• Synthesis and Antitumor Activity of Fused Quinoline Derivatives. V. Methylindolo(3,2-b)quinolines.
  作者：Yasuo TAKEUCHI、Masayuki KITAOMO、Ming-rong CHANG、Shota SHIRASAKA、Chinami SHIMAMURA、Yumiko OKUNO、Masatoshi YAMATO、Takashi HARAYAMA

  DOI：10.1248/cpb.45.2096

  日期：——

  Indolo[3,2-b]quinoline derivatives (1b-i) with a methyl group at each possible position have been synthesized. The 1-methyl (1b) and 9-methyl (1i) derivatives were inactive, but the 3-methyl (1d), 4-methyl (1e), and 6-methyl (1f) derivatives exhibited high treatment/control (T/C) value and cure rates against leukemia P388 in mice. These results indicated that modification of indolo[3,2-b]quinoline

  合成了在每个可能位置具有甲基的吲哚并[3,2-b]喹啉衍生物（1b-i）。1-甲基（1b）和9-甲基（1i）衍生物没有活性，但是3-甲基（1d），4-甲基（1e）和6甲基（1f）衍生物表现出较高的处理/控制（T / C）小鼠抗白血病P388的价值和治愈率。这些结果表明，吲哚[3,2-b]喹啉衍生物在3、4和6位的修饰可能是优化前导的有用方法。
• Condensed quinoline system N-glycosides
  申请人：Mect Corporation

  公开号：US05217961A1

  公开（公告）日：1993-06-08

  The present invention provides condensed quinoline compounds represented by the following general formula (I): ##STR1## in which Z is NH, X is hydrogen, L is lower alkoxy, M is NHQ, Q is --SO.sub.2 CH.sub.3, Y is --NHR, and R is: ##STR2## These compounds are effective for inhibiting KB-cell growth and prolongation of the life span of mice implanted with tumor P-388.

  本发明提供了由以下一般式（I）表示的浓缩喹啉化合物：##STR1## 其中Z为NH，X为氢，L为较低的烷氧基，M为NHQ，Q为--SO.sub.2 CH.sub.3，Y为--NHR，R为：##STR2## 这些化合物对抑制KB细胞生长和延长植入P-388肿瘤的小鼠寿命具有有效性。
• Condensed quinoline system compound and process of preparation thereof
  申请人：MECT CORPORATION

  公开号：EP0376166A1

  公开（公告）日：1990-07-04

  Novel condensed quinoline system compounds such as indenoquinoline system compounds, indoloquinoline system compounds, benzothienoquinoline system compounds and benzofuranoquinoline system compounds, and a process for preparation of these compounds are provided. The present invention is also directed to salts of the above compounds. The compounds of the present invention are effective for inhibition of KB-cell growth and prolongation of life span in cancer implanted mice.

  本发明提供了新型缩合喹啉系化合物，如茚并喹啉系化合物、吲哚并喹啉系化合物、苯并噻吩并喹啉系化合物和苯并呋喃并喹啉系化合物，以及制备这些化合物的工艺。本发明还涉及上述化合物的盐类。本发明的化合物可有效抑制 KB 细胞的生长，延长癌症植入小鼠的寿命。
• 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：——