6-bromo-5-methoxyacetamidoindan-1-one | 501131-86-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 6-bromo-5-methoxyacetamidoindan-1-one
• 英文别名: N-(6-bromo-1-oxo-2,3-dihydroinden-5-yl)-2-methoxyacetamide
• CAS: 501131-86-8
• 化学式: C₁₂H₁₂BrNO₃
• 分子量: 298.136
• InChiKey: KFETZBJQIWSNQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-bromo-5-methoxyacetamidoindan-1-one 在 tris(dibenzylideneacetone)dipalladium (0) 1,1'-双(二苯基膦)二茂铁 、 sodium hydroxide 、 氢溴酸 、 双氧水 、 2,4-滴二甲胺盐 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 生成 2-Hydroxymethyl-7,8-dihydro-3H-cyclopenta[g]quinazoline-4,6-dione
  参考文献：
  名称：

  Cyclopenta[g]quinazolinone-based inhibitors of thymidylate synthase targeting α-folate receptor overexpressing tumours: synthetic approaches to 4-{N-[(6RS)-2-hydroxymethyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino}benzoic acid

  摘要：

  An advanced intermediate for the synthesis of cyclopenta[g]quinazolinone-based antifolates such as (6RS)-CB300945 was prepared by a convergent methodology. The oxo-functionality required for the formation of the C-6-N-10 bond in 4 was introduced in the initial steps of the synthesis, then the tricyclic ring was constructed and finally the propargyl group was introduced using the (propargyl)CO2(CO)(6)(+) complex without the need to protect the N-3-H or 2-hydroxymethyl functionalities. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.092
• 作为产物：
  描述：

  5-methoxyacetamidoindane 在 chromium(VI) oxide 、 溴 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 1.75h， 生成 6-bromo-5-methoxyacetamidoindan-1-one
  参考文献：
  名称：

  Cyclopenta[g]quinazolinone-based inhibitors of thymidylate synthase targeting α-folate receptor overexpressing tumours: synthetic approaches to 4-{N-[(6RS)-2-hydroxymethyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino}benzoic acid

  摘要：

  An advanced intermediate for the synthesis of cyclopenta[g]quinazolinone-based antifolates such as (6RS)-CB300945 was prepared by a convergent methodology. The oxo-functionality required for the formation of the C-6-N-10 bond in 4 was introduced in the initial steps of the synthesis, then the tricyclic ring was constructed and finally the propargyl group was introduced using the (propargyl)CO2(CO)(6)(+) complex without the need to protect the N-3-H or 2-hydroxymethyl functionalities. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.092

文献信息

• [EN] PROCESS FOR THE PREPARATION OF CYCLOPENTA[g]QUINAZOLINE DERIVATIVES<br/>[FR] PROCEDE DE SYNTHESE
  申请人：BTG INT LTD

  公开号：WO2003020706A1

  公开（公告）日：2003-03-13

  Cyclopenta[g]quinazolines of formula (I), and esters and amides thereof may be made by reacting an ester or amide of formula (II), or a protected derivative thereof with a complex containing the (propargyl)Co2(CO)6+ion.

  公式(I)的环戊基[g]喹唑啉，以及其酯和酰胺可以通过将公式(II)的酯或酰胺或其保护衍生物与含有(propargyl)Co2(CO)6+离子的配合物反应而制得。
• [EN] ANTI-CANCER CYCLOPENTA[G]QUINAZOLINE COMPOUNDS<br/>[FR] COMPOSES DE CYCLOPENTA[G]QUINAZOLINE ANTICANCEREUX
  申请人：BTG INT LTD

  公开号：WO2003020748A1

  公开（公告）日：2003-03-13

  Cyclopenta[g]quinazolines of the formula (I):- wherein: A is a group OR or NR0R1 wherein R?0 and R1¿ are each independently hydrogen C¿l-4? alkyl, C3-4 alkenyl, C3-4 alkynyl, C2-4 hydroxyalkyl, C2-4 halogenoalkyl or Cl-4 cyanoalkyl, or R?0 and R1¿ together with the intermediate N form a five- or six-membered heterocyclic ring; p is an integer in the range 1 to 4; R2 is hydrogen, C¿1-4? alkyl, C3-4 alkenyl, C3-4 alkynyl, C2-4 hydroxyalkyl, C2-4 halogenoalkyl or Cl-4 cyanoalkyl; Ar?l¿ is phenylene, thiophenediyl, thiazolediyl, pyridinediyl or pyrimidinediyl which may optionally bear one or two substituents selected from halogeno, hydroxy, amino, nitro, cyano, trifluoromethyl, C¿l-4? alkyl and Cl-4 alkoxy; and R?3¿ is a group of one of the following formulae: -A?1-Ar2-A2-Y1 -A5¿-CON(R)CH(Y?4)Y5 -A8-X-Ar4¿ and pharmaceutically acceptable salts or esters thereof are of therapeutic value particularly in the treatment of cancer.

  式(I)的环戊- [g]喹唑啉：其中：A是OR或NR0R1基团，其中R?0和R1¿各自独立地为氢，C¿l-4?烷基，C3-4烯基，C3-4炔基，C2-4羟基烷基，C2-4卤代烷基或Cl-4氰基烷基，或者R?0和R1¿与中间的N一起形成一个五元或六元杂环；p是1至4之间的整数；R2是氢，C¿1-4?烷基，C3-4烯基，C3-4炔基，C2-4羟基烷基，C2-4卤代烷基或Cl-4氰基烷基；Ar?l¿是苯撑，噻吩二基，噻唑二基，吡啶二基或嘧啶二基，可以选择地带有一个或两个取代基，所选取代基为卤代，羟基，氨基，硝基，氰基，三氟甲基，C¿l-4?烷基和Cl-4烷氧基；R?3¿是以下公式之一的基团：-A?1-Ar2-A2-Y1，-A5¿-CON(R)CH(Y?4)Y5，-A8-X-Ar4¿以及其药学上可接受的盐或酯，在癌症治疗中具有治疗价值。
• Anti-cancer cyclopenta (g)quinazoline compounds
  申请人：——

  公开号：US20040242606A1

  公开（公告）日：2004-12-02

  Cyclopenta[g]quinazolines of the formula (I):- wherein: A is a group OR or NR 0 R 1 wherein R 0 and R 1 are each independently hydrogen C 1-4 alkyl, C 3-4 alkenyl, C 3-4 alkynyl, C 2-4 hydroxyalkyl, C 2-4 halogenoalkyl or C 1-4 cyanoalkyl, or R 0 and R 1 together with the intermediate N form a five- or six-membered heterocyclic ring, p is an integer in the range 1 to 4, R 2 is hydrogen, C 1-4 alkyl, C 3-4 alkenyl, C 3-4 alkynyl, C 2-4 hydroxyalkyl, C 2-4 halogenoalkyl or C 1-4 cyanoalkyl; Ar 1 is phenylene, thiophenediyl, thiazolediyl, pyridinediyl or pyrimidinediyl which may optionally bear one or two substituents selected from halogeno, hydroxy, amino, nitro, cyano, trifluoromethyl, C 1-4 alkyl and C 1-4 alkoxy, and R 3 is a group of one of the following formulae: -A 1 -Ar 2 -A 2 -Y 1 -A 5 -CON(R)CH(Y 4 )Y 5 -A 8 -X—Ar 4 and pharmaceutically acceptable salts or esters thereof are of therapeutic value particularly in the treatment of cancer. 1

  公式（I）的环戊[g]喹唑啉：其中：A是OR或NR0R1基团，其中R0和R1各自独立地为氢、C1-4烷基、C3-4烯基、C3-4炔基、C2-4羟基烷基、C2-4卤代烷基或C1-4氰基烷基，或者R0和R1与中间的N一起形成五元或六元杂环；P是1至4范围内的整数，R2是氢、C1-4烷基、C3-4烯基、C3-4炔基、C2-4羟基烷基、C2-4卤代烷基或C1-4氰基烷基；Ar1是苯基、噻吩基、噻唑基、吡啶基或嘧啶基，其中可以选择带有卤素、羟基、氨基、硝基、氰基、三氟甲基、C1-4烷基和C1-4烷氧基的一个或两个取代基；R3是下列式中的一种基团：-A1-Ar2-A2-Y1-A5-CON(R)CH(Y4)Y5-A8-X—Ar4及其药学上可接受的盐或酯在治疗癌症方面具有治疗价值。
• Process for the preparation of cyclopenta[g]quinazoline derivatives
  申请人：——

  公开号：US20040266798A1

  公开（公告）日：2004-12-30

  Cyclopenta[g]quinazolines of formula (I), and esters and arnides thereof may be made by reacting an ester or amide of formula (II); or a protected derivative thereof with a complex containing the (propargyl)Co 2 (CO) 6 + ion. 1

  公式（I）的环戊[g]喹唑啉及其酯和酰胺可以通过将公式（II）的酯或酰胺或其保护衍生物与含（丙炔基）Co2（CO）6+离子的配合物反应而制得。
• Anti-cancer cyclopenta[G]quinazoline compounds
  申请人：Bavetsias Vasilios

  公开号：US20090023760A1

  公开（公告）日：2009-01-22

  Cyclopenta[g]quinazolines of the formula (I): wherein: A is a group OR or NR 0 R 1 wherein R 0 and R 1 are each independently hydrogen C 1-4 alkyl, C 1-4 alkenyl, C 1-4 alkynyl, C 1-4 hydroxyalkyl, C 1-4 halogenoalkyl or C 1-4 cyanoalkyl, or R 0 and R 1 together with the intermediate N form a five- or six-membered heterocyclic ring, p is an integer in the range 1 to 4, R 2 is hydrogen C 1-4 alkyl, C 1-4 alkenyl, C 1-4 alkynyl, C 1-4 hydroxyalky,. C 2-4 halogenoalkyl or C 1-4 cyanoalkyl; Ar 1 is phenylene, thiophenediyl, amino, nitro, cyano, trifluoromethyl, C -4 alkyl and C 1-4 alkoxy, and R 3 is a group of one of the following formulae: -A 1 -Ar 2 -A 2 -Y 1 -A 5 -CON(R)(R)CH(Y 4 )Y 5 -A 6 -X-Ar 4 and pharmaceutically acceptable salts or esters thereof are of therapeutic value particularly in the treatment of cancer.

  公式（I）的环戊基[g]喹唑啉化合物：其中：A是OR或NR0R1基团，其中R0和R1各自独立地为氢，C1-4烷基，C1-4烯基，C1-4炔基，C1-4羟基烷基，C1-4卤代烷基或C1-4氰基烷基，或者R0和R1与中间的N一起形成五元或六元杂环；p是1到4之间的整数，R2是氢，C1-4烷基，C1-4烯基，C1-4炔基，C1-4羟基烷基，C2-4卤代烷基或C1-4氰基烷基；Ar1是苯基，噻吩基，氨基，硝基，氰基，三氟甲基，C-4烷基和C1-4烷氧基，R3是以下公式之一的基团：-A1-Ar2-A2-Y1-A5-CON（R）（R）CH（Y4）Y5-A6-X-Ar4及其药学上可接受的盐或酯具有治疗价值，特别是用于治疗癌症。