7,8-dihydro-6H-cyclopenta[g]quinazoline | 1059158-67-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 7,8-dihydro-6H-cyclopenta[g]quinazoline
• CAS: 1059158-67-6
• 化学式: C₁₁H₁₀N₂
• 分子量: 170.214
• InChiKey: BQQULWSGZOLQLV-UHFFFAOYSA-N

物化性质

• 熔点：
  97-98 °C
• 沸点：
  322.4±11.0 °C(predicted)
• 密度：
  1.223±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7,8-dihydro-6H-cyclopenta[g]quinazoline 、 1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 methyl 6-(6-amino-2,3-dihydro-1H-inden-5-yl)-1,4,5,6-tetrahydro-4-oxopyridine-3-carboxylate
  参考文献：
  名称：

  基于环化/环裂解程序的2-（2-氨基苯基）-2,3-二氢吡啶-4（1H）-one的高效合成

  摘要：

  （苄氧羰基）保护的3,4-苯并-7-羟基-2,9-二氮杂双环[3.3.1] non-7-烯是通过1,3-双（甲硅烷基烯醇醚）与喹唑啉的一锅环化制备的。随后的氢化导致一锅脱保护和重排，得到2-（2-氨基苯基）-2,3-二氢吡啶-4-4 （1 H）-。

  DOI：

  10.1002/hlca.201100130
• 作为产物：
  描述：

  ethyl N-(2,3-dihydro-1H-inden-5-yl)carbamate 、 乌洛托品 在 三氟乙酸 、 氢氧化钾 、 potassium ferricyanide 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以0.910 g的产率得到7,8-dihydro-6H-cyclopenta[g]quinazoline
  参考文献：
  名称：

  Synthesis of 3,4-benzo-7-hydroxy-2,9-diazabicyclo[3.3.1]non-7-enes by cyclization of 1,3-bis(silyl enol ethers) with quinazolines

  摘要：

  通过1,3-双(硅烯醇醚)与喹唑啉的单锅环化反应，制备了一系列功能化的3,4-苯并-7-羟基-2,9-二氮杂双环[3.3.1]诺烯。环化的机制通过B3LYP/6-31G(d)密度泛函理论计算进行了研究。产物可以通过铃木交叉偶联反应进行功能化。1,3-双(硅烯醇醚)与邻苯二胺的反应则产生开链而非环化产物。

  DOI：

  10.1039/b803141j

文献信息

• 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。
• Anti-cancer cyclopenta [G] quinazoline compounds
  申请人：Bavetsias Vassilios

  公开号：US20100056551A1

  公开（公告）日：2010-03-04

  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.

  公式（I）的环戊基[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R0和R1与中间的N一起形成五元或六元杂环；p是在1到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是苯撑、噻吩二基、噻唑二基、吡啶二基或嘧啶二基，可选地带有一或两个取自卤代、羟基、氨基、硝基、氰基、三氟甲基、C1-4烷基和C1-4烷氧基的取代基；以及R3是下列公式之一的基团：-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。
• Anti-cancer cyclopenta [G]quinazonline compounds
  申请人：Bavetsias Vasilios

  公开号：US20100216824A1

  公开（公告）日：2010-08-26

  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.

  式（I）中的环戊二十二碳五烯基喹唑啉：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到4之间的整数；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是苯撑基、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卤代、羟基、氨基、硝基、氰基、三氟甲基、C1-4烷基和C1-4烷氧基的取代基；以及R3是以下公式之一的基团：-A1-Ar2-A2-Y1-A5-CON(R)CH(Y4)Y5-A8-X—Ar4和其药学上可接受的盐或酯对于治疗癌症具有治疗价值。
• Anti-cancer cyclopenta(g)quinazoline compounds
  申请人：Bavetsias Vassilios

  公开号：US20100273817A1

  公开（公告）日：2010-10-28

  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.

  公式（I）的环戊基[g]喹唑啉：其中：A是OR或NR0R1基团，其中R0和R1各自独立地是氢，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，或者R0和R1与中间的N一起形成五元或六元杂环；p是在1到4之间的整数；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，所述取代基选自卤代，羟基，氨基，硝基，氰基，三氟甲基，C1-4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）CH（Y4）Y5-A8-X—Ar4和其药学上可接受的盐或酯在治疗癌症方面具有治疗价值。
• CYCLOPENTAQUINAZOLINE DERIVATIVES FOR THE TREATMENT OF RHEUMATOID ARTHRITIS OR ACUTE MYELOID LEUKAEMIA
  申请人：Jansen Gerrit

  公开号：US20110190211A1

  公开（公告）日：2011-08-04

  A cyclopenta[g]quinazoline derivative, containing an L-Glu-γ-D-Glu dipeptide group, of formula (I): wherein R 1 is amino, C 1-4 hydroxyalkyl, C 1-4 fluoroalkyl or methoxy-C 1-4 -alkyl; 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; and Ar 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, the compound (I) optionally being in the form of a pharmaceutically acceptable salt or ester; may be used for the treatment of rheumatoid arthritis or acute myeloid leukaemia.