1-chloro-4,5-dimethyl-8-methoxy-5H-pyrido[4,3-b]-indole | 111380-54-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-chloro-4,5-dimethyl-8-methoxy-5H-pyrido[4,3-b]-indole
• 英文别名: chloro-1 dimethyl-4,5 methoxy-8-5H-pyrido <4,3-b> indole；1-chloro-8-methoxy-4,5-dimethyl-5H-pyrido<4,3-b>indole；1-chloro-4,5-dimethyl-8-methoxy-5H-pyrido(4,3-b)indole；1-Chloro-8-methoxy-4,5-dimethylpyrido[4,3-b]indole
• CAS: 111380-54-2
• 化学式: C₁₄H₁₃ClN₂O
• 分子量: 260.723
• InChiKey: DEXYJDQNEXTELS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-chloro-4,5-dimethyl-8-methoxy-5H-pyrido[4,3-b]-indole 在 氢溴酸 作用下， 生成 1-(3-diethylamino propylamino)-4,5-dimethyl-8-hydroxy-5H-pyrido[4,3-b]indole
  参考文献：
  名称：

  1-Amino-substituted 4-methyl-5H-pyrido[4,3-b]indoles (.gamma.-carbolines) as tricyclic analogs of ellipticines: a new class of antineoplastic agents

  摘要：

  A series of 1-amino-substituted 4-methyl-5H-pyrido[4,3-b]indoles that are structurally related to ellipticines by deletion of a ring have been synthesized in order to evaluate their DNA affinity, their in vitro cytotoxicity on L1210 cultured cells, and their in vivo antitumor activity. Among 24 derivatives that have been prepared and studied for the structure-activity relationship in this new class of antineoplastic agents, those that have a NH(CH2)3N(R)2 side chain (R = CH3 or C2H5) at their 1-position, a 4-methyl group, and an 8-OH substituent, either with a 5-NH or with a 5-NCH3 group, show the most potent cytotoxicities on L1210 cultured cells and in vivo antitumor properties in P388 and L1210 leukemia systems. In vivo antineoplastic activity of the most potent products was confirmed in P388 and L1210 leukemia systems. In vivo antineoplastic activity of the most potent products was confirmed on other mouse experimental tumors from the standard NCI screening:B16 melanoma and C38 adenocarcinoma.

  DOI：

  10.1021/jm00397a023
• 作为产物：
  描述：

  6,7,8,9-tetrahydro-8-methoxy-4-methyl-2H,5H-pyrido<4,3-b>indol-1-one 在 palladium on activated charcoal 、 potassium carbonate 、 三氯氧磷 作用下， 以 二苯醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 73.0h， 生成 1-chloro-4,5-dimethyl-8-methoxy-5H-pyrido[4,3-b]-indole
  参考文献：
  名称：

  1-Amino-substituted 4-methyl-5H-pyrido[4,3-b]indoles (.gamma.-carbolines) as tricyclic analogs of ellipticines: a new class of antineoplastic agents

  摘要：

  A series of 1-amino-substituted 4-methyl-5H-pyrido[4,3-b]indoles that are structurally related to ellipticines by deletion of a ring have been synthesized in order to evaluate their DNA affinity, their in vitro cytotoxicity on L1210 cultured cells, and their in vivo antitumor activity. Among 24 derivatives that have been prepared and studied for the structure-activity relationship in this new class of antineoplastic agents, those that have a NH(CH2)3N(R)2 side chain (R = CH3 or C2H5) at their 1-position, a 4-methyl group, and an 8-OH substituent, either with a 5-NH or with a 5-NCH3 group, show the most potent cytotoxicities on L1210 cultured cells and in vivo antitumor properties in P388 and L1210 leukemia systems. In vivo antineoplastic activity of the most potent products was confirmed in P388 and L1210 leukemia systems. In vivo antineoplastic activity of the most potent products was confirmed on other mouse experimental tumors from the standard NCI screening:B16 melanoma and C38 adenocarcinoma.

  DOI：

  10.1021/jm00397a023

文献信息

• Synthèse d'analogues tricycliques des ellipticines : les methyl-4,5h-pyrido [4,3-b] indoles (γ-carbolines) diversement substttus sur leurs sommets 1,5 et 8.
  作者：Chi Hung Nguyen、Emile Bisagni

  DOI：10.1016/s0040-4020(01)89985-3

  日期：1987.1

  Several ways to 1-functionnalized 4-methyl-5H-pyrido [ 4,3-b ] indoles have been worked out:

  已经找到了几种将1-官能化的4-甲基-5H-吡啶基[4,3-b]吲哚方法：
• Derivatives of pyridoindole, having anti-tumor properties
  申请人：Sanofi

  公开号：US04835160A1

  公开（公告）日：1989-05-30

  The present invention concerns derivatives of 5H-pyrido[4,3-b]-indole with the following general formula: ##STR1## in which n represents a whole number from 2 to 4, R.sub.1 represents hydrogen or a lower alkyl group; R.sub.2 represents hydrogen, a hydroxy group or a lower alkyloxy group; R.sub.3 and R.sub.4 represents hydrogen, a lower alkyl group or hydroxyalkyl group, R.sub.5 can be identical or different and represents hydrogen, a hydroxy group or a lower alkyl group, as well as the tautomeric forms and the addition salts with pharmaceutically acceptable mineral or organic acids. The invention also concerns their preparation process, and their use as medicaments.

  本发明涉及5H-吡啶并[4,3-b]-吲哚的衍生物，其具有以下通用式：##STR1## 其中n表示2至4的整数，R.sub.1表示氢或较低的烷基基团；R.sub.2表示氢，羟基或较低的烷氧基；R.sub.3和R.sub.4表示氢，较低的烷基或羟基烷基，R.sub.5可以相同或不同，表示氢，羟基或较低的烷基，以及与药学上可接受的矿物质或有机酸的加合物的互变异构体形式。本发明还涉及它们的制备过程以及它们作为药物的用途。
• 1,2-dihydro-4-methyl-1-oxo-5H-pyrido(4,3-b)indoles and the process for
  申请人：Sanofi and Centre National De La Recherche Scientifique

  公开号：US04870180A1

  公开（公告）日：1989-09-26

  The present invention relates to new compounds which are the 1,2-dihydro-4-methyl-1-oxo-5H-pyrido(4,3-b)indoles with the formula (I): ##STR1## in which R represents hydrogen or an alkoxy or aryl carbonyloxy group. These compounds are intermediates of synthesis in the preparation of compounds which can be used in the pharamaceutical industry. The invention is also concerned with their synthesis.

  本发明涉及新化合物，为具有以下式子的1,2-二氢-4-甲基-1-氧代-5H-吡咯[4,3-b]吲哚(I)：##STR1## 其中R代表氢或烷氧基或芳香羰氧基。这些化合物是制备可用于制药工业中的化合物的合成中间体。本发明还涉及它们的合成。
• BISAGNI, EMILE;CHI, HUNG NGUYEN;DE, COINTET PAUL
  作者：BISAGNI, EMILE、CHI, HUNG NGUYEN、DE, COINTET PAUL

  DOI：——

  日期：——
• BISAGNI, EMILE;NGUYEN, CHI HUNG;PIERRE, ALAIN;PEPIN, ODILE;COINTET, PAUL +, J. MED. CHEM., 31,(1988) N 2, 398-405
  作者：BISAGNI, EMILE、NGUYEN, CHI HUNG、PIERRE, ALAIN、PEPIN, ODILE、COINTET, PAUL +

  DOI：——

  日期：——