1-chloro-8-hydroxy-4-methyl-5H-pyrido<4,3-b>indole | 111380-53-1

• 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-8-hydroxy-4-methyl-5H-pyrido<4,3-b>indole
• 英文别名: chloro-1 methyl-4 hydroxy-8-5H-pyrido <4,3-b> indole；1-chloro-8-hydroxy-4-methyl-5H-pyrido[4,3-b]indole；1-Chloro-4-methyl-5h-pyrido[4,3-b]indol-8-ol
• CAS: 111380-53-1
• 化学式: C₁₂H₉ClN₂O
• 分子量: 232.669
• InChiKey: YGQWULILSFWCRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  48.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-二甲基-1,3-二氨基丙烷 、 1-chloro-8-hydroxy-4-methyl-5H-pyrido<4,3-b>indole 以78%的产率得到(γ-dimethylamino)propylamino-1 methyl-4 hydroxy-8-5H-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：

  chloro-1 methyl-4 benzoyloxy-8-5H-pyrido <4,3-b> indole 在 氨 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以80.4%的产率得到1-chloro-8-hydroxy-4-methyl-5H-pyrido<4,3-b>indole
  参考文献：
  名称：

  玫瑰树碱合成类似物：4,5h-吡啶甲基[4,3-b]吲哚（γ-咔啉）甲基变体亚砜类混合物1,5等。

  摘要：

  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：

  DOI：

  10.1016/s0040-4020(01)89985-3

文献信息

• 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。
• 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：——
• US4835160A
  申请人：——

  公开号：US4835160A

  公开（公告）日：1989-05-30
• [EN] 5H-PYRIDO[4,3-B]INDOLE DERIVATIVE COMPOUNDS AND USES THEREOF AS MEDICINE FOR TREATING POLYGLUTAMIN NEURODEGENERATIVE DISEASES<br/>[FR] COMPOSES DERIVES DE 5H-PYRIDO[4,3-B]INDOLE ET LEURS UTILISATIONS COMME MEDICAMENT POUR TRAITER LES MALADIES NEURODEGENERATIVES A POLYGLUTAMINES
  申请人：TROPHOS

  公开号：WO2006125887A1

  公开（公告）日：2006-11-30

  [EN] The invention concerns the treatment of neurodegenerative diseases. More particularly, it concerns a family of compounds derived from 5H-pyrido [4,3-b] indole for which a neuroprotecting activity has been shown. The invention concerns those novel products, their synthesis methods as well as certain likewise novel synthesis intermediates. The invention also concerns compositions comprising the compounds of said family, the use of said compounds as drugs, in particular for preparing a medicine for treating polyglutamin neurodegenerative diseases.
  [FR] La présente invention se place dans le domaine du traitement des maladies neurodégénératives. Très particulièrement elle concerne une famille de composés dérivés de 5H-pyrido [4,3-b] indole pour lesquelles une activité neuroprotectrice a pu être démontrée. L'invention concerne ces produits nouveaux, leurs procédé de synthèse ainsi que certains intermédiaires de synthèse eux-mêmes nouveaux. La présente invention concerne également des compositions comprenant les composés de la famille, l'utilisation desdits composés à titre de médicaments, particulièrement dans la préparation d'un médicament destiné au traitement des maladies neurodégénératives à polyglutamines.