2-(cyclohexylcarbonyl)-1,2,3,4,6,7,12,12b-octahydropyrazino[2,1-a]β-carbolin-4-one | 106412-95-7

• 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: 2-(cyclohexylcarbonyl)-1,2,3,4,6,7,12,12b-octahydropyrazino[2,1-a]β-carbolin-4-one
• 英文别名: 4-(Cyclohexanecarbonyl)-4,7,17-triazatetracyclo[8.7.0.02,7.011,16]heptadeca-1(10),11,13,15-tetraen-6-one
• CAS: 106412-95-7
• 化学式: C₂₁H₂₅N₃O₂
• 分子量: 351.448
• InChiKey: LGHVEXQZVBLBAA-UHFFFAOYSA-N

物化性质

• 熔点：
  260-267 °C
• 沸点：
  637.3±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 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：

  2-(cyclohexylcarbonyl)-1,2,3,4,6,7,12,12b-octahydropyrazino[2,1-a]β-carbolin-4-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以76%的产率得到2-cyclohexylmethyl-1,2,3,4,6,7,12,12b-octahydropyrazino<1',2':1,2>pyrido<3,4-b>indole
  参考文献：
  名称：

  Synthesis and hypotensive activities of octahydropyrazino[1′,2′:1,2]pyrido[3,4-b]indoles and 15-azayohimbanes

  摘要：

  The hypotensive activities in rats of indolic compounds 1-9 were compared with that of reserpine. In spite of differences in their structure, all 9 showed similar hypotensive activities to that of reserpine. New octahydropyrazinopyridoindoles 3-6 and the tetrahydro-beta-carboline 7 were synthesized.

  DOI：

  10.1016/0223-5234(94)90114-7
• 作为产物：
  描述：

  4,9-二氢-3H-吡啶并(3,4-B)吲哚 在 吡啶 、 氢气 、 三氟乙酸 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 41.0h， 生成 2-(cyclohexylcarbonyl)-1,2,3,4,6,7,12,12b-octahydropyrazino[2,1-a]β-carbolin-4-one
  参考文献：
  名称：

  Synthesis of new praziquantel analogues: Potential candidates for the treatment of schistosomiasis

  摘要：

  An efficient synthesis of antischistosomal drug praziquantel and analogues was achieved and the synthetic route designed was to afford structurally diverse analogues for better structure-activity relationship understanding. Total of nineteen PZQ analogues with structural variations at amide, piperazine and aromatic moieties have been synthesized and fully characterized. Among all the new analogues tested for antischistosomal activity, one dimethoxy tetrahydroisoquinoline analogue and two tetrahydro-beta-carboline analogues exhibited moderate activity against adult Schistosoma mansoni. Tetrahydro-beta-carboline analogues showed moderate activity whereas the presence of p-trifluoromethylbenzoyl and p-toluenesulphonyl moieties resulted in complete suppression of antischistosomal activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.108

文献信息

• NMR spectroscopy of hexa- and octahydropyrazino [1′, 2′ : 1,2]pyrido [3,4-b]indoles and 15-azayohimbanes
  作者：Nativitat Valls、Victor M. Segarra、Josep Bonjoch

  DOI：10.1002/mrc.1260291003

  日期：1991.10

  The 1H (200 MHz) and 13C (50.3 MHz) NMR spectra of some hexa‐ and octahydropyrazino[1′, 2′ : 1,2]pyrido‐[3,4‐b]indoles (1–13), 15‐azayohimbanes (15–18), and related compounds (14, 19, 20) are reported. The data have been analyzed in terms of the preferred conformation (9–13, 15–20) and configuration (15–20).

  一些六氢和八氢吡嗪并 [1', 2' : 1,2] pyrido-[3,4-b]indoles (1-13), 15-azayohimbanes 的 1H (200 MHz) 和 13C (50.3 MHz) NMR 光谱(15–18) 和相关化合物 (14, 19, 20) 被报道。已根据首选构象 (9–13, 15–20) 和构型 (15–20) 对数据进行了分析。
• Efficient and Diverse Synthesis of Indole Derivatives
  作者：Haixia Liu、Alexander Dömling

  DOI：10.1021/jo900986z

  日期：2009.9.4

  A convergent 2-step procedure toward an array of indole derivatives involving an Ugi reaction and a Pictet-Spengler reaction is described. The reactions are versatile regarding different starting materials. Hexacyclic 24 can be produced with unprecedented complexity.
• Valls, Nativitat; Segarra, Victor M.; Bosch, Joan, Heterocycles, 1986, vol. 24, # 4, p. 943 - 946
  作者：Valls, Nativitat、Segarra, Victor M.、Bosch, Joan

  DOI：——

  日期：——
• VALLS N.; SEGARRA V. M.; BOSCH J., HETEROCYCLES, 24,(1986) N 3, 943-946
  作者：VALLS N.、 SEGARRA V. M.、 BOSCH J.

  DOI：——

  日期：——
• Synthesis of new praziquantel analogues: Potential candidates for the treatment of schistosomiasis
  作者：Partha Sarathi Sadhu、Singam Naveen Kumar、Malapaka Chandrasekharam、Livia Pica-Mattoccia、Donato Cioli、Vaidya Jayathirtha Rao

  DOI：10.1016/j.bmcl.2011.11.108

  日期：2012.1

  An efficient synthesis of antischistosomal drug praziquantel and analogues was achieved and the synthetic route designed was to afford structurally diverse analogues for better structure-activity relationship understanding. Total of nineteen PZQ analogues with structural variations at amide, piperazine and aromatic moieties have been synthesized and fully characterized. Among all the new analogues tested for antischistosomal activity, one dimethoxy tetrahydroisoquinoline analogue and two tetrahydro-beta-carboline analogues exhibited moderate activity against adult Schistosoma mansoni. Tetrahydro-beta-carboline analogues showed moderate activity whereas the presence of p-trifluoromethylbenzoyl and p-toluenesulphonyl moieties resulted in complete suppression of antischistosomal activity. (C) 2011 Elsevier Ltd. All rights reserved.