2-methyl-7,8,9,10-tetrahydrocyclohepta[b]indol-6(5H)-one

• 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-methyl-7,8,9,10-tetrahydrocyclohepta[b]indol-6(5H)-one
• 英文别名: 7-methyl-1-oxo-1,2,3,4,5,10-hexahydrocyclohept[b]indole；7,8,9,10-Tetrahydro-2-methylcyclohepta[b]indol-6(5H)-one；2-methyl-7,8,9,10-tetrahydro-5H-cyclohepta[b]indol-6-one
• 化学式: C₁₄H₁₅NO
• 分子量: 213.279
• InChiKey: WWOUENIGFSSADG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methyl-7,8,9,10-tetrahydrocyclohepta[b]indol-6(5H)-one 在 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 30.0h， 生成 2-hydroxy-9-methyl-5,6,7,12-tetrahydropyrimido[5',6':6,7]cyclohepta[b]indole
  参考文献：
  名称：

  Synthesis, antimicrobial, antimycobacterial and structure–activity relationship of substituted pyrazolo-, isoxazolo-, pyrimido- and mercaptopyrimidocyclohepta[b]indoles

  摘要：

  A new class of heterocycles, specifically substituted pyrazolo-, isoxazolo- and pyrimidocyclohepta[b]indoles, has been prepared by condensation of substituted 7-(hydroxymethylene)-7,8,9,10-tetrahydrocyclohepta[b]indol-6(5H)-ones with hydrazine hydrate, hydroxylamine hydrochloride, phenylhydrazine, urea and thiourea, respectively. The structures of the compounds were established by IR, H-1 NMR, C-13 NMR, mass spectral analysis, X-ray diffraction, and the compounds have been screened for in vitro antimicrobial and antimycobacterial against Mycobacterium tuberculosis H37Rv (MTB). Among the compounds screened, five substances were found to have an MIC of 3.12 mu g/ml or greater against MTB. Structure-activity relationship (SAR) analyses and in silico drug relevant properties (HBD, HBA, PSA, c Log P, M.wt) confirmed that the compounds are potential lead compounds for future drug discovery studies. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.046
• 作为产物：
  描述：

  2-(p-methylphenylamino)cyclohept-2-enone 在 三乙胺 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 2,2,2-三氟乙醇 为溶剂， 以42%的产率得到2-methyl-7,8,9,10-tetrahydrocyclohepta[b]indol-6(5H)-one
  参考文献：
  名称：

  Synthesis of substituted tetrahydron-1H-carbazol-1-one and analogs via PhI(OCOCF3)2-mediated oxidative C–C bond formation

  摘要：

  A variety of tetrahydro-1H-carbazol-1-ones and analogs were conveniently synthesized from the reaction of the corresponding 2-(phenylamino)cyclohex-2-enone with hypervalent iodine reagent PhI(OCOCF3)2 (FIFA), through a direct intramolecular oxidative C(sp(2))-C(sp(2)) bond formation. This approach realized the construction of the biologically important tetrahydro-1H-carbazol-1-one and tetrahydrocyclohepta[b]lindol-6(5H)-one skeletons. The mechanism of the process was proposed and briefly discussed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.02.083

文献信息

• Structural Investigations on 4-Chloro-6-Phenyl-7,8,9,14-Tetrahydroquinolino [2′,3′:7,6]cyclohept[b]indoles
  作者：Ezhumalai Yamuna、Makuteswaran Sridharan、Karnam Jayarampillai Rajendra Prasad、Matthias Zeller

  DOI：10.1007/s10870-009-9668-z

  日期：2010.5

  8,9,14-tetrahydroquinolino[2′,3′:7,6]cyclohept[b]indole derivatives were obtained in one pot synthesis reactions via acid catalyzed condensation and cyclization of 1-oxo-1,2,3,4,5,10-hexahydrocyclohept[b]indoles with 2-amino-5-chlorobenzophenone in glacial acetic acid. Parent 4-chloro-6-phenyl-7,8,9,14-tetrahydroquinolino[2′,3′:7,6]cyclohept[b]indole and the 10, 11, 12 and 13-methyl derivatives all

  通过一锅合成反应，通过酸催化缩合和环化1获得了几种4-氯-6-苯基-7,8,9,14-四氢喹啉[2',3':7,6]环庚[b]吲哚衍生物-oxo-1,2,3,4,5,10-六氢环庚[b]吲哚与2-氨基-5-氯二苯甲酮在冰醋酸中。母体 4-氯-6-苯基-7,8,9,14-四氢喹啉[2',3':7,6]环庚[b]吲哚和10、11、12和13-甲基衍生物均在三斜空间群 P$$ \overline1} $$。11-甲基衍生物结晶时Z'=2，10-甲基异构体和12-甲基异构体共结晶为两个分子的固溶体，13-甲基衍生物和母体化合物各自的Z'=1。 晶胞参数对于四个结构是 a = 10.1826(8), b = 12.3918(7), c = 16.3825(8)Å, α = 91.626(1), β = 95.718(1), γ = 94.966(1)° 和 V = 2,047。7(2) Å3 为 11
• Synthesis, Spectral Analysis, Molecular Docking and Biological Evaluation of Cyclohepta[b]indole Derivatives
  作者：Ayyachamy Pandian Amuthavalli、Babu Prakash、David Edison、Rajendran Velmurugan

  DOI：10.5562/cca3375

  日期：——

  A new series of specifically substituted cyclohepta[b]indole derivatives from the precursor thiophen-2-ylmethylene has been synthesized. The structures of synthesized derivatives were established by spectral and elemental analyses. The docking studies with protein kinase CK2 was performed, derivative 6c exhibited the most excellent glide and E model score of –7.61 and –58.27, respectively. In-vitro anticancer activity against cervical cancer cell line (HeLa) was studied. The IC50 values were compared with the standard drug Ellipticine. Compounds 5c, 6c and 6d showed better IC50 value when compared to the other molecules. The derivatives were evaluated for their antibacterial activity against the reference drugs Sparfloxacin and Norfloxacin using agar dilution method. The derivatives 4a–d exhibited better MIC values against Gram-positive bacteria and Gram-negative bacteria when compared with remaining derivatives. Structure activity relationship (SAR) analyses established that the derivatives are potential lead compounds for future drug development studies.

  一系列新的特定取代的环庚[b]吲哚衍生物从前体硫代苯基亚甲基合成。合成衍生物的结构通过光谱和元素分析确定。进行了与蛋白激酶CK2的对接研究，衍生物6c表现出最优秀的滑动和E模型得分分别为-7.61和-58.27。研究了对宫颈癌细胞系（HeLa）的体外抗癌活性。IC50值与标准药物Ellipticine进行了比较。与其他分子相比，化合物5c、6c和6d显示出更好的IC50值。使用琼脂稀释法评估了衍生物对参考药物Sparfloxacin和Norfloxacin的抗菌活性。与其余衍生物相比，衍生物4a-d对革兰氏阳性菌和革兰氏阴性菌的MIC值更好。结构活性关系（SAR）分析确定这些衍生物是未来药物开发研究的潜在先导化合物。
• Synthesis of thieno- and benzocyclohepta[b]indoles: Gewald reaction and regioselective cycloaddition of acetylenic esters
  作者：Ezhumalai Yamuna、Matthias Zeller、Philip O. Adero、Karnam Jayaramapillai Rajendra Prasad.

  DOI：10.3998/ark.5550190.0013.630

  日期：——

  An efficient two-step method for the synthesis of thienoand benzocyclohepta[b]indole derivatives, starting from 7,8,9,10-tetrahydrocyclohepta[b]indole-6(5H)-one, is reported. The procedures are simple and show a remarkable tolerance towards the presence of functional groups such as e.g. amines, carbonitriles or methoxycarbonyl substituents.

  报道了一种从 7,8,9,10-四氢环庚烷 [b]indole-6(5H)-one 开始合成噻吩并苯并环庚烷 [b] 吲哚衍生物的有效两步法。该程序简单并且对官能团的存在显示出显着的耐受性，例如胺、腈或甲氧基羰基取代基。
• Synthesis of Quinolino[2′,3′:7,6]Cyclohept[b]Indoles and their Antimicrobial Activities
  作者：Ezhumalai Yamuna、Karnam Jayarampillai Rajendra Prasad

  DOI：10.3184/030823410x520769

  日期：2010.7

  Practicable and concise syntheses of 6-chloro-7,8,9,14-tetrahydroquinolino[2′,3′:7,6]cyclohept[b]indoles by two routes are described. Both commenced with 1-oxo-2,3,4,5,10-hexahydrocyclohept[b]indoles and utilised either the acid-catalysed condensation with 2-aminobenzonitrile, followed by treatment with POCl₃ or, better, direct condensation of the ketone with anthranilic acid in POCl₃.

  本论文介绍了通过两种途径简明实用地合成 6-氯-7,8,9,14-四氢喹啉并[2′,3′:7,6]环庚烷并[b]吲哚的方法。这两种方法都以 1-氧代-2,3,4,5,10-六氢环庚烷并[b]吲哚为起点，利用酸催化与 2-氨基苯甲腈缩合，然后用 POCl3 处理，或者更好的方法是在 POCl3 中直接缩合酮与蒽酸。
• Elegant One-Pot Synthesis of Quinolino[2′,3′:7,6]-cyclohept[1,2-<i>b</i>]indole Through Friedländer and Pfitzinger Annulation Reaction
  作者：Ezhumalai Yamuna、Anthony Yurcho、Robert J. Sovesky、Peter M. Smith、Matthias Zeller、Karnam Jayarampillai Rajendra Prasad

  DOI：10.1080/00397911.2010.518048

  日期：2011.11.15

  A rapid, simple, and efficient method for the preparation of various quinolino[2',3': 7,6] cyclohept[1,2-b]indoles has been developed through the Friedlander and Pfitzinger condensations of 1-oxo-cyclohept[b]indole with o-amino benzophenone and isatin respectively. Reactions were performed by under different reaction conditions.