Trans-2,3,6,7,12,12a-hexahydro-2-benzyl-6-phenyl-pyrazino[2',1';6,1]pyrido[3,4-b]indole-1,4-dione | 1224845-00-4

• 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: Trans-2,3,6,7,12,12a-hexahydro-2-benzyl-6-phenyl-pyrazino[2',1';6,1]pyrido[3,4-b]indole-1,4-dione
• 英文别名: (2S,8S)-6-benzyl-2-phenyl-3,6,17-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),11,13,15-tetraene-4,7-dione
• CAS: 1224845-00-4
• 化学式: C₂₇H₂₃N₃O₂
• 分子量: 421.499
• InChiKey: QOLYEMQAJKMMHC-OZXSUGGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  56.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Trans-2,3,6,7,12,12a-hexahydro-2-benzyl-6-phenyl-pyrazino[2',1';6,1]pyrido[3,4-b]indole-1,4-dione 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 3.0h， 以96%的产率得到(6S,12aR)-2-benzyl-2,3,6,7,12,12a-hexahydro-6-phenyl-pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione
  参考文献：
  名称：

  他达拉非样四环化合物立体发散合成的有效通用方法

  摘要：

  他达拉非样四环化合物的 C-12a 位的清洁和通用 DBU 催化差向异构化已得到充分研究。此外，通过使用这种干净的差向异构化作为关键步骤，从 L - 和 D - 色氨酸甲酯盐酸盐和氘代胡椒醛立体发散合成了 6-d 1 - 他达拉非的四种立体异构体。

  DOI：

  10.1002/ejoc.200901378
• 作为产物：
  描述：

  D-色氨酸乙酯盐酸盐 在 碳酸氢钠 作用下， 以 乙醇 、 乙酸乙酯 、 苯 为溶剂， 反应 72.5h， 生成 Trans-2,3,6,7,12,12a-hexahydro-2-benzyl-6-phenyl-pyrazino[2',1';6,1]pyrido[3,4-b]indole-1,4-dione
  参考文献：
  名称：

  Synthesis of Functionalized Diketopiperazines as Cyclotryprostatin and Tryprostatin Analogues

  摘要：

  Various ketopiperazines were synthesized as (cyclo) tryprostatin analogues. Construction of the skeleton started with a Pictet-Spengler reaction followed by acylation or alkylation of the piperidine nitrogen and condensation with a primary amine. 2-Chloroacetyl tetrahydro-beta-carbolines rearranged towards the corresponding 2-chloro-N-[2-(1H-indol-3-yl)ethyl]acetamide derivatives upon treatment with NBS. These compounds were cyclized with primary amines towards the corresponding functionalized diketopiperazines.

  DOI：

  10.1055/s-0032-1316911

文献信息

• Tetracyclic cyclic GMP-specific phosphodiesterase inhibitors, process of
  申请人：ICOS Corporation

  公开号：US06143746A1

  公开（公告）日：2000-11-07

  A compound of formula (I) and salts and solvates thereof, in which: R.sup.0 represents hydrogen, halogen, or C.sub.1-6 alkyl; R.sup.1 represents hydrogen, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, haloC.sub.1-6 alkyl, C.sub.3-8 cycloalkyl, C.sub.3-8 cycloalkylC.sub.1-3 alkyl, arylC.sub.1-3 alkyl, or heteroarylC.sub.1-3 alkyl; R.sup.2 represents an optionally substituted monocyclic aromatic ring selected from benzene, thiophene, furan, and pyridine, or an optionally substituted bicyclic ring (a) attached to the rest of the molecule via one of the benzene ring carbon atoms, and wherein the fused ring (A) is a 5- or 6-membered ring which may be saturated or partially or fully unsaturated, and comprises carbon atoms and optionally one or two heteroatoms selected from oxygen, sulphur, and nitrogen; and R.sup.3 represents hydrogen or C.sub.1-3 alkyl, or R.sup.1 and R.sup.3 together represent a 3- or 4-membered alkyl or alkenyl chain. A compound of formula (I) is a potent and selective inhibitor of cyclic guanosine 3',5'-monophosphate specific phosphodiesterase (cGMP specific PDE) having a utility in a variety of therapeutic areas where such inhibition is beneficial, including the treatment of cardiovascular disorders and erectile dysfunction.

  化合物的公式为(I)，其盐和溶剂化物，其中：R.sup.0代表氢，卤素或C.sub.1-6烷基；R.sup.1代表氢，C.sub.1-6烷基，C.sub.2-6烯基，C.sub.2-6炔基，卤C.sub.1-6烷基，C.sub.3-8环烷基，C.sub.3-8环烷基C.sub.1-3烷基，芳基C.sub.1-3烷基或杂环芳基C.sub.1-3烷基；R.sup.2代表一种选择自苯，噻吩，呋喃和吡啶中的可选择性取代的单环芳香环，或者是一个可选择性取代的双环环（a），通过苯环碳原子之一连接到分子的其余部分，其中融合的环（A）是一个5-或6-成员环，可以是饱和的或部分或完全不饱和的，并包括碳原子和可选择性的一个或两个氧、硫和氮的杂原子；R.sup.3代表氢或C.sub.1-3烷基，或R.sup.1和R.sup.3一起代表一个3-或4-成员烷基或烯基链。公式(I)的化合物是环鸟苷3'，5'-单磷酸特异性磷酸二酯酶（cGMP特异性PDE）的有效和选择性抑制剂，具有在多种治疗领域中有益的抑制作用，包括心血管疾病和勃起功能障碍的治疗。
• Tetracyclic derivatives, process of preparation and use
  申请人：ICOS Corporation

  公开号：US20020119976A1

  公开（公告）日：2002-08-29

  A compound of formula (I) 1 and salts and solvates thereof, in which: R o represents hydrogen, halogen or C 1-6 alkyl; R 1 represents hydrogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, halo C 1-6 alkyl, C 3-8 cycloalkyl, C 3-8 cycloalkyl C 1-3 alkyl, arylC 1-3 alkyl or heteroaryl C 1-3 alkyl; R 2 represents an optionally substituted monocyclic aromatic ring selected from benzene, thiophene, furan and pyridine or an optionally substituted bicyclic ring 2 attached to the rest of the molecule via one of the benzene ring carbon atoms and wherein the fused ring A is a 5- or 6-membered ring which may be saturated or partially or fully unsaturated and comprises carbon atoms and optionally one or two heteroatoms selected from oxygen, sulphur and nitrogen; and R 3 represents hydrogen or C 1-3 alkyl, or R 1 and R 3 together represent a 3- or 4-membered alkyl or alkenyl chain. A compound of formula (I) is a potent and'selective inhibitor of cyclic guanosine 3′, 5′-monophosphate specific phosphodiesterase (CGMP specific PDE) having a utility in a variety of therapeutic areas where such inhibition is beneficial, including the treatment of cardiovascular disorders.

  式(I)1的化合物及其盐和溶剂化物，其中：R代表氢，卤素或C1-6烷基；R1代表氢，C1-6烷基，C2-6烯基，C2-6炔基，卤代C1-6烷基，C3-8环烷基，C3-8环烷基C1-3烷基，芳基C1-3烷基或杂环芳基C1-3烷基；R2代表一个可选的取代的单环芳香环，选择自苯，噻吩，呋喃和吡啶或一个可选的取代的二环2，通过苯环碳原子之一连接到分子的其余部分，其中融合的环A是一个5-或6-成员环，可以是饱和的或部分或完全不饱和的，并包括碳原子和可选的一个或两个异原子，选择自氧，硫和氮；R3代表氢或C1-3烷基，或R1和R3一起代表一个3-或4-成员烷基或烯基链。式(I)的化合物是环鸟苷3'，5'-单磷酸特异性磷酸二酯酶（CGMP特异性PDE）的有效和选择性抑制剂，具有在多种治疗领域中抑制有益的功效，包括心血管疾病的治疗。
• Method of inhibiting neoplastic cells with tetracyclic pyrido[3,4-B] indole derivatives
  申请人：——

  公开号：US20020035111A1

  公开（公告）日：2002-03-21

  A method for inhibiting neoplasia, particularly cancerous and precancerous lesions by exposing the affected cells to pyrido[3,4b]indoles.

  一种通过将受影响的细胞暴露于吡啶并［3,4b］吲哚来抑制肿瘤，特别是癌症和癌前病变的方法。
• US5859006A
  申请人：——

  公开号：US5859006A

  公开（公告）日：1999-01-12
• US6025494A
  申请人：——

  公开号：US6025494A

  公开（公告）日：2000-02-15