(+/-)-cis-1-p-tolyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester | 81727-12-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: (+/-)-cis-1-p-tolyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester
• 英文别名: methyl (1R,3R)-1-(4-methylphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 81727-12-0；81727-13-1；82789-32-0
• 化学式: C₂₀H₂₀N₂O₂
• 分子量: 320.391
• InChiKey: BEEVAEJHPKFYMA-QZTJIDSGSA-N

物化性质

• 沸点：
  502.5±50.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-cis-1-p-tolyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 在 三乙胺 作用下， 以 乙醇 为溶剂， 生成 (2R,8R)-6-[(3R)-1-benzylpyrrolidin-3-yl]-2-(4-methylphenyl)-3,6,17-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),11,13,15-tetraene-4,7-dione
  参考文献：
  名称：

  Design, synthesis and biological activity of β-carboline-based type-5 phosphodiesterase inhibitors

  摘要：

  The SAR of a series of beta-carboline derived type 5 phosphodiesterase inhibitors has been explored and we have discovered compounds with excellent levels of PDE5 potency and selectivity over PDE6. However, the series exhibits low levels of selectivity over PDE11, a phosphodiesterase with unknown function. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00159-8
• 作为产物：
  描述：

  DL-色氨酸 在 氯化亚砜 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 (+/-)-cis-1-p-tolyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Syntheses of new substituted triazino tetrahydroisoquinolines and β-carbolines as novel antileishmanial agents1

  摘要：

  A series of triazino tetrahydroisoquinolines (3-5) and beta-carboline derivatives (15-27) have been synthesized as novel antileishmanial agents. Among them, compounds 15, 16 and 25 have shown 78.0%, 78.6% and 68.0% in vivo inhibition against Leishmania donovani at a dose of 50 mg kg(-1) x 5 days, respectively, while compounds 3 and 18 exhibited 55.6% and 53.3% in vivo inhibitions, respectively, against L. donovani at a dose of 50 mg kg(-1) x 5 days. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.09.007

文献信息

• Identification of Novel Amino Acid Derived CCK-2R Antagonists As Potential Antiulcer Agent: Homology Modeling, Design, Synthesis, and Pharmacology
  作者：Amit K. Gupta、Kanika Varshney、Neetu Singh、Vaibhav Mishra、Mridula Saxena、Gautam Palit、Anil K. Saxena

  DOI：10.1021/ci3003655

  日期：2013.1.28

  homology model of CCK-2R using human A2a adenosine receptor and the resolved NMR based structure of the third extracellular loop of the CCK-2R as templates. Further in order to identify novel antiulcer agents, rational designing have been performed utilizing the substructure of a well-known CCK-2R antagonist benzotript as a lead molecule and submitted to the combined docking and simulation studies. This

  本研究使用人类A 2a重新研究了CCK-2R的三维（3D）同源性模型腺苷受体和CCK-2R第三细胞外环的基于NMR的解析结构作为模板。此外，为了鉴定新的抗溃疡剂，已经利用公知的CCK-2R拮抗剂苯并三联体的亚结构作为前导分子进行了合理的设计，并进行了联合的对接和模拟研究。这导致了对小分子CCK-2R拮抗剂构象异构体的基本结构要求以及结合模式的变化的理解。在下一步中，进行这些分子的每种构型异构体的制备并提交其体外活性，然后在体内筛选成抗溃疡大鼠模型。6a是一种口服活性安全候选分子，具有比众所周知的苯并三唑更好的抗溃疡特性。
• Synthesis of Tadalafil Analogues
  作者：Liu‐Tang Wang、Hao Huang、Zhong‐Lin Ye、Yong Wu、Xue‐Chao Wang

  DOI：10.1080/00397910600764626

  日期：2006.9
• Synthesis and cytotoxicity evaluation of (tetrahydro-β-carboline)-1,3,5-triazine hybrids as anticancer agents
  作者：Ravi Kumar、Leena Gupta、Pooja Pal、Shahnawaz Khan、Neetu Singh、Sanjay Babu Katiyar、Sanjeev Meena、Jayanta Sarkar、Sudhir Sinha、Jitendra Kumar Kanaujiya、Savita Lochab、Arun Kumar Trivedi、Prem M.S. Chauhan

  DOI：10.1016/j.ejmech.2010.02.001

  日期：2010.6

  A series of tetrahydro-beta-carbolines and 1,3,5-triazine hybrids have been synthesized and evaluated for their cytotoxicity against a panel of eight human cancer cell lines and normal human fibroblasts (NIH3T3). It led us to discovery of racemic compounds 69, 71 and 75, which are selectively cytotoxic towards KB (oral cancer) cell line with IC(50) values of 1058, 664 7 and 122.2 nM, respectively, while their enantiopure forms are less active and not selective. Enantiopure compound 42 showed 2 5 times more selectivity towards MCF7 cells over normal fibroblast NIH3T3 cells with an IC(50) value of 740 nM, also arrests cell cycle in G(1) phase and induces apoptosis in MCF7 and MDA MB231cell lines.
• KUMAR, SHIV;SETH, M.;BHADURI, A. P., INDIAN J. CHEM., 1982, 20, N 12, 1078-1079
  作者：KUMAR, SHIV、SETH, M.、BHADURI, A. P.

  DOI：——

  日期：——
• Design, synthesis and biological activity of β-carboline-based type-5 phosphodiesterase inhibitors
  作者：Graham N. Maw、Charlotte M.N. Allerton、Eugene Gbekor、William A. Million

  DOI：10.1016/s0960-894x(03)00159-8

  日期：2003.4

  The SAR of a series of beta-carboline derived type 5 phosphodiesterase inhibitors has been explored and we have discovered compounds with excellent levels of PDE5 potency and selectivity over PDE6. However, the series exhibits low levels of selectivity over PDE11, a phosphodiesterase with unknown function. (C) 2003 Elsevier Science Ltd. All rights reserved.