10-Methoxy-7-methyl-7H-pyrido[4,3-c]carbazole | 62099-90-5

• 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: 10-Methoxy-7-methyl-7H-pyrido[4,3-c]carbazole
• 英文别名: 7H-Pyrido(4,3-c)carbazole, 10-methoxy-7-methyl-；10-methoxy-7-methylpyrido[4,3-c]carbazole
• CAS: 62099-90-5
• 化学式: C₁₇H₁₄N₂O
• 分子量: 262.311
• InChiKey: OHTQLXBHKUSFLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  10-Methoxy-7-methyl-7H-pyrido[4,3-c]carbazole 、 1-(2-chloroeth-1-yl)-1'-<2-<(6-chloro-2-methoxy-9-acridinyl)amino>eth-1-yl>-4,4'-bipiperidine 生成 6-chloro-2-methoxy-N-[2-[4-[1-[2-(10-methoxy-7-methylpyrido[4,3-c]carbazol-2-ium-2-yl)ethyl]piperidin-4-yl]piperidin-1-yl]ethyl]acridin-9-amine;chloride;dihydrochloride
  参考文献：
  名称：

  LEON, P.;GARBAY-JAUREGUIBERRY, C.;LAMBERT, B.;LE, PECQ J. B.;ROQUES, B. P+, J. MED. CHEM., 31,(1988) N 5, 1021-1026

  摘要：

  DOI：
• 作为产物：
  描述：

  10-甲氧基-7H-吡啶并(4,3-c)咔唑 、 碘甲烷 在 sodium hydride 作用下， 生成 10-Methoxy-7-methyl-7H-pyrido[4,3-c]carbazole
  参考文献：
  名称：

  DNA intercalating compounds as potential antitumor agents. 1. Preparation and properties of 7H-pyridocarbazoles

  摘要：

  The DNA intercalating compounds derived from 6H-pyridocarbazole (ellipticines, olivacines) elicit high antitumor properties. In order to get information about the mechanism of action of these agents it is necessary to study structurally related analogues. For this purpose, various derivatives of the four isomeric 7H-pyridocarbazoles were synthesized by a single photochemical process on indolylpyridylethylenes. These derivatives are able to intercalate into DNA. The DNA binding affinities vary in the range of 10(4) to 10(6) M-1, depending mainly on the nature of the substituent, nitrogen quaternization being the most enhancing factor. The position of the pyridinic nitrogen does not markedly affect the DNA binding affinity. Three quaternized compounds elicit a significative but low antileukemic activity on L1210 mice leukemia. The properties of 7H-pyridocarbazoles are discussed and compared to those of 6H-pyridocarbazoles (ellipticines and olivacines).

  DOI：

  10.1021/jm00186a009

文献信息

• Asymmetrical bisintercalators as potential antitumor agents
  作者：P. Leon、C. Garbay-Jaureguiberry、B. Lambert、J. B. Le Pecq、B. P. Roques

  DOI：10.1021/jm00400a023

  日期：1988.5

  dimeric molecules made up of two identical 7H-pyrido[4,3-c]carbazole rings linked by symmetrical linking chains. These dimers elicit antitumor properties through a new mechanism of action. Recently, a relationship was found between their antitumor properties and their cytotoxic effect on the polA Escherichia coli mutant strain, suggesting that 7H-pyrido[4,3-c]carbazole dimers might induce a DNA deformation

  Ditercalinium及其类似物是由通过对称连接链连接的两个相同的7H-吡啶并[4,3-c]咔唑环组成的二聚体分子。这些二聚体通过新的作用机理引发抗肿瘤特性。最近，发现它们的抗肿瘤特性与对polA大肠杆菌突变株的细胞毒性作用之间存在关联，这表明7H-吡啶并[4,3-c]咔唑二聚体可能会诱导可被大肠杆菌识别的DNA变形。 SOS修复系统。因此，在本研究中，通过在结构中引入不对称参数，研究了对称性在二萜类似物中的DNA结合，抗肿瘤特性和细菌毒性的作用。二聚体要么通过不对称刚性连接链合成，要么由两种化学上不同的生色团组成，即 cr啶和7H-吡啶并[4,3-c]咔唑。不对称的二聚体仍然能够以高亲和力双插入到DNA中，但是观察到它们的抗肿瘤能力急剧下降。另一方面，这些不对称二聚体对polA大肠杆菌突变体（如其对称类似物）具有细胞毒性。这些结果表明，对称性在7H-吡啶并[4,3-c]咔唑二聚体系列的抗肿瘤效力中起着至关重要的作用。
• LEON, P.;GARBAY-JAUREGUIBERRY, C.;LAMBERT, B.;LE, PECQ J. B.;ROQUES, B. P+, J. MED. CHEM., 31,(1988) N 5, 1021-1026
  作者：LEON, P.、GARBAY-JAUREGUIBERRY, C.、LAMBERT, B.、LE, PECQ J. B.、ROQUES, B. P+

  DOI：——

  日期：——
• LEON, P.;GARBAY-JAUREGUIBERRY, C.;BARSI, M. C.;LE, PECQ J. B.;ROQUES, B. +, J. MED. CHEM., 30,(1987) N 11, 2074-2080
  作者：LEON, P.、GARBAY-JAUREGUIBERRY, C.、BARSI, M. C.、LE, PECQ J. B.、ROQUES, B. +

  DOI：——

  日期：——
• DNA intercalating compounds as potential antitumor agents. 1. Preparation and properties of 7H-pyridocarbazoles
  作者：Didier Pelaprat、Robert Oberlin、Irene Le Guen、Jean Bernard Le Pecq、Bernard P. Roques

  DOI：10.1021/jm00186a009

  日期：1980.12

  The DNA intercalating compounds derived from 6H-pyridocarbazole (ellipticines, olivacines) elicit high antitumor properties. In order to get information about the mechanism of action of these agents it is necessary to study structurally related analogues. For this purpose, various derivatives of the four isomeric 7H-pyridocarbazoles were synthesized by a single photochemical process on indolylpyridylethylenes. These derivatives are able to intercalate into DNA. The DNA binding affinities vary in the range of 10(4) to 10(6) M-1, depending mainly on the nature of the substituent, nitrogen quaternization being the most enhancing factor. The position of the pyridinic nitrogen does not markedly affect the DNA binding affinity. Three quaternized compounds elicit a significative but low antileukemic activity on L1210 mice leukemia. The properties of 7H-pyridocarbazoles are discussed and compared to those of 6H-pyridocarbazoles (ellipticines and olivacines).