6-bromo-7-bromoethyl[1,3]dioxolo[4,5-g]quinoline | 536711-61-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-bromo-7-bromoethyl[1,3]dioxolo[4,5-g]quinoline
• 英文别名: 2-bromo-3-bromomethyl-6,7-methylenedioxy-quinoline；6-Bromo-7-(bromomethyl)-[1,3]dioxolo[4,5-g]quinoline
• CAS: 536711-61-2
• 化学式: C₁₁H₇Br₂NO₂
• 分子量: 344.99
• InChiKey: GLMJLVBTEHEAMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-bromo-7-bromoethyl[1,3]dioxolo[4,5-g]quinoline 生成 7-Ethyl-7-hydroxy-2,3-methylenedioxy-9,12-dihydro-7H-cyclopenta [6,7]indolizino[,1,2-b]quinoline-8,10-dione
  参考文献：
  名称：

  Camptothecin analogue compounds

  摘要：

  化合物的化学式为（I）：其中，n为0、1或2，R1代表（C3-C11）环烷基或（C3-C11）环烷基烷基，R2、R3、R4和R5选自氢、卤素、烷基、烯基、炔基、全氟烷基、环烷基、环烷基烷基、羟基、羟基烷基、烷氧基、烷氧基烷基、烷氧羰基、酰氧基、羧基、硝基、氰基、氨基羰基（可选取代）和（CH2）p-NaRb和-O-C（O）-N-RaRb等基团，其中p、Ra和Rb的定义如说明书所述，或者相邻的两个基团R2、R3、R4和R5组成-O-（CH2）t-O基团，其中t为1到3的整数，R60、R70n、R80和R90代表氢原子、羟基、烷氧基或如说明书中所定义的O-（CO）-X或O-（CO）-NXW基团，R61、R71n、R81和R91代表氢原子、烷基、烯基或炔基，或成对地结合成键或环氧基团，或两个基团共同形成一个酮基团。含有这些化合物的药物对治疗癌症有用。

  公开号：

  US06699876B2
• 作为产物：
  描述：

  6-氯[1,3]二噁唑[4,5-g]喹啉-7-甲醛 在 sodium tetrahydroborate 、 三溴化磷 作用下， 以 乙醇 、 苯 为溶剂， 反应 37.5h， 生成 6-bromo-7-bromoethyl[1,3]dioxolo[4,5-g]quinoline
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 10,11-Methylenedioxy-14-azacamptothecin

  摘要：

  10,11-Methylenedioxy-14-azacamptothecin, a potent analogue of the antitumor agent camptothecin (CPT), has been prepared via a key condensation between AB and DE ring precursors. The biological testing of this compound validated a strategy for modulation of the off-rate of camptothecin analogues from the topoisomerase-DNA-CPT ternary complex via structural modification.

  DOI：

  10.1021/ol0611604

文献信息

• Camptothecin Analogue Compounds, a Process for Their Preparation and Pharmaceutical Compositions Containing Them
  申请人：Lavielle Gilbert

  公开号：US20100168149A1

  公开（公告）日：2010-07-01

  Compound of formula (I): wherein: R 1 , R 2 , R 3 , R 4 , R 5 , R 80 , R 90 , R 81 , R 91 , Alk and G are as defined in the description. Medicinal products containing the same which are useful in the treatment of cancer diseases.

  化合物的式子（I）：其中：R1，R2，R3，R4，R5，R80，R90，R81，R91，Alk和G如描述中所定义。含有此类化合物的药物产品在癌症治疗中有用。
• Camptothecin Analogue Compounds, a Process for Their Preparation and Pharmaceutical Compositions Containing Them.
  申请人：Lavielle Gilbert

  公开号：US20100168150A1

  公开（公告）日：2010-07-01

  Compound of formula (I): wherein: R 1 , R 2 , R 3 , R 4 , R 5 , R 80 , R 90 , R 81 , R 91 , Alk, Alk′, X, X′ and G are as defined in the description. Medicinal products containing the same which are useful in the treatment of cancer diseases.

  化合物的公式（I）：其中：R1、R2、R3、R4、R5、R80、R90、R81、R91、Alk、Alk'、X、X'和G的定义如说明书所述。包含该化合物的药物产品在治疗癌症疾病方面具有用途。
• Synthesis and pharmacological evaluation of novel non-lactone analogues of camptothecin
  作者：Patrick Hautefaye、Bernard Cimetière、Alain Pierré、Stéphane Léonce、John Hickman、William Laine、Christian Bailly、Gilbert Lavielle

  DOI：10.1016/s0960-894x(03)00534-1

  日期：2003.8

  Ten novel camptothecin (CPT) derivatives devoid of the lactone function in the E-ring were synthesized and evaluated as anticancer agents. Several of these CPT analogues bearing a five-membered E-ring are potent inhibitors of the DNA relaxation and cleavage reactions catalyzed by topoisomerase I and exhibit promising cytotoxic activities with IC(50) values in the nM range. This is the first successful

  合成了十个在E环中没有内酯功能的新型喜树碱（CPT）衍生物，并将其评估为抗癌剂。这些带有五元E环的CPT类似物中的几种是拓扑异构酶I催化的DNA松弛和裂解反应的有效抑制剂，并显示出有希望的细胞毒活性，其IC（50）值在nM范围内。这是无内酯的CPT的第一个成功设计，因此为拓扑异构酶I靶向抗肿瘤药的开发提供了新途径。
• New camptothecin analogue compounds
  申请人：——

  公开号：US20020077325A1

  公开（公告）日：2002-06-20

  Compound of formula (I): 1 wherein: n is 0, 1 or 2, R 1 , R 2 , R 3 , R 4 and R 5 are selected from hydrogen, halogen, alkyl, alkenyl, alkynyl, perhaloalkyl, cycloalkyl, cycloalkylalkyl, hydroxy, hydroxyalkyl, alkoxy, alkoxyalkyl, alkoxycarbonyl, acyloxy, carboxy, nitro, cyano, aminocarbonyl (optionally substituted), and the groups (CH 2 ) p —NR a R b and —O—C(O)—N—R a R b , with p, R a and R b being as defined in the description, or two adjacent groups R 2 , R 3 , R 4 and R 5 together form a group —O—(CH 2 ) t —O, t being an integer from 1 to 3), R 60 , R 70n , R 80 and R 90 represent a hydrogen atom, a hydroxy group, an alkoxy group, or an O—(CO)—X or O—(CO)—NXW group as defined in the description, R 61 , R 71n , R 81 and R 91 represent a hydrogen atom , alkyl, alkenyl or alkynyl, or taken in pairs together form a bond or an oxirane group, or two groups together form an oxo group. and medicinal products containing the same are useful for the treatment of cancerous diseases.

  化合物的式子（I）：其中：n为0、1或2，R1、R2、R3、R4和R5选择自氢、卤素、烷基、烯基、炔基、全氟烷基、环烷基、环烷基烷基、羟基、羟基烷基、烷氧基、烷氧基烷基、烷氧羰基、酰氧基、羧基、硝基、氰基、氨基羰基（可选择性取代），以及(CH2)p-NRaRb和-O-C(O)-N-RaRb这些基团，其中p、Ra和Rb如描述中所定义，或者相邻的两个基团R2、R3、R4和R5共同形成一个-O-(CH2)t-O的基团，其中t为1到3的整数。R60、R70n、R80和R90代表氢原子、羟基、烷氧基或描述中定义的O-(CO)-X或O-(CO)-NXW基团。R61、R71n、R81和R91代表氢原子、烷基、烯基或炔基，或者成对地共同形成键或环氧丙烷基团，或者两个基团共同形成一个羰基团。含有这些化合物的药品对于治疗癌症疾病是有用的。
• New campothecin analogue compounds
  申请人：——

  公开号：US20030105109A1

  公开（公告）日：2003-06-05

  Compound of formula (I): 1 wherein: n is 0, 1 or 2, R 1 represents (C 3 -C 11 )cycloalkyl or (C 3 -C 11 )cycloalkylalkyl, R 2 , R 3 , R 4 and R 5 are selected from hydrogen, halogen, alkyl, alkenyl, alkynyl, perhaloalkyl, cycloalkyl, cycloalkylalkyl, hydroxy, hydroxyalkyl, alkoxy, alkoxyalkyl, alkoxycarbonyl, acyloxy, carboxy, nitro, cyano, aminocarbonyl (optionally substituted), and the groups (CH 2 ) p —N a R b and —O—C(O)—N—R a R b , with p, R a and R b being as defined in the description, or two adjacent groups R 2 , R 3 , R 4 and R 5 together form a group —O—(CH 2 ) t —O, t being an integer from 1 to 3, R 60 , R 70n , R 80 and R 90 represent a hydrogen atom, a hydroxy group, an alkoxy group, or an O—(CO)—X or O—(CO)—NXW group as defined in the description, R 61 , R 71n , R 81 , and R 91 represent a hydrogen atom, alkyl, alkenyl or alkynyl, or taken in pairs together form a bond or an oxirane group, or two groups together form an oxo group. and medicinal products containing the same are useful for the treatment of cancerous disesases.

  式(I)的化合物： 其中： n为0、1或2， R1代表(C3-C11)环烷基或(C3-C11)环烷基烷基， R2、R3、R4和R5选择自氢、卤素、烷基、烯基、炔基、全卤烷基、环烷基、环烷基烷基、羟基、羟基烷基、烷氧基、烷氧基烷基、烷氧羰基、酰氧基、羧基、硝基、氰基、氨基羰基（可选地取代）和(CH2)p—NaRb和—O—C(O)—N—RaRb基团，其中p、Ra和Rb如描述中定义，或者相邻的两个基团R2、R3、R4和R5组成—O—(CH2)t—O基团，其中t为1到3的整数， R60、R70n、R80和R90代表氢原子、羟基、烷氧基，或者如描述中所定义的O—(CO)—X或O—(CO)—NXW基团， R61、R71n、R81和R91代表氢原子、烷基、烯基或炔基，或成对地共同形成键或环氧基团，或两个基团共同形成氧基团。 含有该化合物的药物对治疗癌症有用。