ethyl-9-methyl-1-phenyl-9H-pyrido[3,4-b]indole-3-carboxylate | 142272-76-2

• 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: ethyl-9-methyl-1-phenyl-9H-pyrido[3,4-b]indole-3-carboxylate
• 英文别名: ethyl 9-methyl-1-phenyl-β-carboline-3-carboxylate；Ethyl 9-methyl-1-phenylpyrido[3,4-b]indole-3-carboxylate
• CAS: 142272-76-2
• 化学式: C₂₁H₁₈N₂O₂
• 分子量: 330.386
• InChiKey: ZAGHTZGXBRYRMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl-9-methyl-1-phenyl-9H-pyrido[3,4-b]indole-3-carboxylate 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 7.0h， 生成 (4-(2-chlorophenyl)piperazin-1-yl)(9-methyl-1-phenyl-9H-pyrido[3,4-b]indol-3-yl)methanone
  参考文献：
  名称：

  Design, synthesis of new β-carboline derivatives and their selective anti-HIV-2 activity

  摘要：

  In the present study, a new series of beta-carboline derivatives were synthesized and evaluated for inhibition activity against both HIV-1 and HIV-2 strains. Among these reported analogues, surprisingly (1-phenyl-9H-pyrido[3,4-b] indol-3-yl)(4-p-tolylpiperazin-1-yl) methanone (7b), (4-(2-methoxyphenyl) piperazin-1-yl)(1-phenyl-9H-pyrido[3,4-b] indol-3-yl) methanone (7f), (4-(4-fluorophenyl) piperazin-1-yl) (1-phenyl-9H-pyrido[3,4-b] indol-3-yl) methanone (7k), (4-(2-fluorophenyl) piperazin-1-yl)(1-phenyl-9H-pyrido[3,4-b] indol-3-yl) methanone (7l) displayed selective inhibition of HIV-2 strain with EC50 values of 3.3, 3.2, 2.6 and 5.4 mu M, respectively, which are comparable with nucleoside reverse transcriptase inhibitors lamivudine and dideoxyinosine. As these analogues have not shown in vitro HIV-2 reverse transcriptase inhibition, it could be excluded as potential target for their specific anti-HIV-2 activity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.01.058
• 作为产物：
  描述：

  ethyl 2,3,4,9-tetrahydro-1-phenyl-1H-pyrido[3,4-b]indole-3-carboxylate 在 sodium hydride 、 sulfur 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 ethyl-9-methyl-1-phenyl-9H-pyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of piperazine group-linked bivalent β-carbolines as potential antitumor agents

  摘要：

  一系列具有3-亚甲基单元之间的哌嗪基间隔的二价β-咔啉类化合物被合成，并评估了它们的体外细胞毒活性。化合物7e和7g表现出强大的细胞毒活性。

  DOI：

  10.1039/c5md00312a

文献信息

• Biological evaluation and structure activity relationship of 9-methyl-1-phenyl-9H-pyrido[3,4-b]indole derivatives as anti-leishmanial agents
  作者：Penta Ashok、Subhash Chander、Terry K. Smith、Rajnish Prakash Singh、Prabhat Nath Jha、Murugesan Sankaranarayanan

  DOI：10.1016/j.bioorg.2018.11.037

  日期：2019.3

  respectively) and amastigotes (EC50 1.4, 1.9 and 2.6 µM respectively). SAR studies revealed that, para substitution of methoxy, chloro groups and methyl group on ortho position favored anti-leishmanial activity against L. infantum. Among these analogues 7d, 7h, 7n and 7g exhibited potent inhibition against L. donovani promastigotes (EC50 0.91, 4.0, 4.57 and 5.02 µM respectively), axenic amastigotes

  通过分子杂交方法设计了一系列哌嗪基-β-咔啉-3-羧酰胺衍生物。合成，表征了设计的类似物，并评估了其对婴儿利什曼原虫和多形利什曼原虫的抗利什曼原虫活性。在婴儿乳杆菌的抑制测定中，化合物7d，7g和7c对前鞭毛体（分别为EC50 1.59、1.47和3.73 µM）和变形虫（EC50分别为1.4、1.9和2.6 µM）显示出有效的抑制作用。SAR研究表明，邻位甲氧基，氯基和甲基的对位取代有利于抗婴儿利什曼原虫的活性。在这些类似物7d，7h，7n和7g中，它们显示出对多诺氏乳杆菌前鞭毛体（分别为EC50 0.91、4.0、4.57和5.02μM），轴突性吻合动物（EC50为0.9、3.5、2.2和3）的有效抑制作用。分别为8 µM）和胞内变形虫（EC50分别为1.3、7.8、5.6和6.3 µM）。SAR研究表明，甲氧基的对位取代，氯基的对位和间位取代以及苄基取代被推荐用于对多诺氏乳杆菌有显着的抗利什曼肽作用。
• Synthesis and preliminary evaluation of novel alkyl diamine linked bivalent β-carbolines as angiogenesis inhibitors
  作者：Liang Guo、Wei Chen、Wenxi Fan、Qin Ma、Rongqin Sun、Guang Shao、Rihui Cao

  DOI：10.1039/c6md00360e

  日期：——

  A series of novel bivalent β-carbolines were synthesized and evaluated as potent angiogenesis inhibitors.

  一系列新颖的双价β-咔啉类化合物被合成并评估为有效的血管生成抑制剂。
• 3位哌嗪桥连接的双β-咔啉碱类化合物及其制 药用途
  申请人：新疆华世丹药物研究有限责任公司

  公开号：CN106349257B

  公开（公告）日：2019-07-12

  本发明公开了3位哌嗪桥连接的双β‑咔啉碱类化合物、其制法和其药物组合物与用途。具体而言，所述的双β‑咔啉碱类化合物及其可药用盐如通式I所述，这类双β‑咔啉碱类化合物的制备是通过β‑咔啉中间体和吡啶缩合。本发明还公开了一种药物组合物，包括有效剂量的式I所示双β‑咔啉碱类化合物和药效学上可接受的载体，以及这类双β‑咔啉碱类化合在制备抗肿瘤药物中的应用，包括黑色素瘤、口腔表皮癌、食道癌、胃癌、肺癌、乳腺癌、肾癌、肝癌、宫颈癌、卵巢癌、胰腺癌、前列腺癌、结肠癌、膀胱癌。
• Design, synthesis and evaluation of diarylpiperazine derivatives as potent anti-tubercular agents
  作者：Ashok Penta、Scott Franzblau、Baojie Wan、Sankaranarayanan Murugesan

  DOI：10.1016/j.ejmech.2015.10.024

  日期：2015.11

  Molecular hybridization is an emerging approach to design novel ligands by combination of two or more pharmacophoric subunits of known bioactive compounds. In the present study, we have designed a novel series of diarylpiperazine analogues, synthesized, characterized using FTIR, H-1 NMR, Mass, Elemental analysis and evaluated their in-vitro anti-tubercular activity. Among the reported sixteen diarylpiperazines, eleven analogues exhibited significant anti-tubercular activity against Mycobacterium tuberculosis H37Rv strain with MIC values below 6.25 mu g/mL and good selectivity index. Structure activity relationship studies concluded that, ortho-para directing group (except para chloro) substitution on ortho and para position of piperazine attached phenyl ring favored anti-tubercular activity. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Van Broeck; Van Doren; Hoornaert, Synthesis, 1992, # 5, p. 473 - 476
  作者：Van Broeck、Van Doren、Hoornaert

  DOI：——

  日期：——