6-methyl-6H-[1,2,3,4,5]pentathiepino[6,7-b]indole | 371970-71-7

• 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: 6-methyl-6H-[1,2,3,4,5]pentathiepino[6,7-b]indole
• 英文别名: 6H-1,2,3,4,5-Pentathiepino[6,7-b]indole, 6-methyl-；6-methylpentathiepino[6,7-b]indole
• CAS: 371970-71-7
• 化学式: C₉H₇NS₅
• 分子量: 289.491
• InChiKey: XFAGGRCHHRNULP-UHFFFAOYSA-N

物化性质

• 熔点：
  123-125 °C
• 沸点：
  549.8±42.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-methyl-6H-[1,2,3,4,5]pentathiepino[6,7-b]indole 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以89%的产率得到5,10-dihydro-5,10-dimethyl[1,2,3,4]-tetrathiocino[5,6-b:8,7-b']diindole
  参考文献：
  名称：

  Reactions of 2-lithiated indoles with elemental sulfur. Formation of pentathiepino[6,7-b]indoles and indoline-2-thiones

  摘要：

  The reactions of 2-lithiated indole and 1-methylindole with elemental sulfur have been studied, leading e.g. to a rational approach to pentathiepino[6,7-b]indoles 5 and 10. Notable amounts of the previously known tetrathiocino[5,6-b:8,7-b ' ]diindole 11 could be observed as a side reaction in the preparation of 10. Treatment of the anions of indoline-2-thiones 6 or 7 with sulfur also gave the pentathiepins 5 or 10, respectively. In addition, a convenient and clean lithiation route to indoline-2-thione (6) has been developed. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00660-3
• 作为产物：
  描述：

  1-甲基吲哚 在 bis(4-aza-1-azoniabicyclo[2.2.2]oct-1-yl)disulfide dichloride 作用下， 以 氯仿 为溶剂， 反应 48.0h， 以51%的产率得到6-methyl-6H-[1,2,3,4,5]pentathiepino[6,7-b]indole
  参考文献：
  名称：

  Regioselective synthesis of pentathiepines fused with pyrrole, thiophene, or indole rings

  摘要：

  通过相应的杂环化合物或其四氢衍生物与预先制备的硫单氯化物和DABCO混合物反应，获得了与吡咯、噻吩或吲哚环融合的Pentathiepines。

  DOI：

  10.1007/s11172-006-0551-1

文献信息

• Regioselective synthesis of pentathiepines fused with pyrrole, thiophene, or indole rings
  作者：L. S. Konstantinova、S. A. Amelichev、O. A. Rakitin

  DOI：10.1007/s11172-006-0551-1

  日期：2006.11

  Pentathiepines fused with pyrrole, thiophene, or indole rings were obtained by reactions of the corresponding heterocycles or their tetrahydro derivatives with a prepared mixture of sulfur monochloride and DABCO.

  通过相应的杂环化合物或其四氢衍生物与预先制备的硫单氯化物和DABCO混合物反应，获得了与吡咯、噻吩或吲哚环融合的Pentathiepines。
• A one-step synthesis of fused pentathiepinsElectronic supplementary information (ESI) available: characterization of compounds 2–5, 9, and 11. See http://www.rsc.org/suppdata/cc/b2/b203349f/
  作者：Lidia S. Konstantinova、Oleg A. Rakitin、Charles W. Rees

  DOI：10.1039/b203349f

  日期：2002.5.17

  Treatment of nucleophilic heterocycles like pyrroles and thiophene, and their tetrahydro derivatives, with S2Cl2 and a base in chloroform at room temperature provides a simple one-pot synthesis of heterocyclic fused mono and bis pentathiepins such as 2, 3, 4, 5, 9, and 11.

  在室温下用S2Cl2和氯仿中的碱处理诸如吡咯和噻吩之类的亲核杂环及其四氢衍生物，可以简单地一锅合成杂环稠合的单和双五硫平，例如2,3、4、5、9，和11。
• Direct synthesis of fused 1,2,3,4,5-pentathiepins
  作者：Stanislav A. Amelichev、Lidia S. Konstantinova、Konstantin A. Lyssenko、Oleg A. Rakitin、Charles W. Rees

  DOI：10.1039/b508186f

  日期：——

  Treatment of nucleophilic heterocycles like pyrroles and thiophenes, and their tetrahydro derivatives, with S2Cl2 and DABCO in chloroform at room temperature provides a simple one-pot synthesis of fused mono and bispentathiepins. N-Methylpyrrole and its 2-chloro and 2,5-dichloro derivatives and N-methylpyrrolidine all give the same dichloropentathiepin 1a. N-Ethyl, isopropyl and tert-butylpyrrolidine behave similarly; the isopropylpyrrolidine also gives the bispentathiepin 6 which undergoes an intriguing rearrangement to the symmetrical monopentathiepin 1c. N-Methyl and ethyl indole give either 2,3-dichloro derivatives 8 or the pentathiepinoindoles 9, depending upon the reaction conditions. Thiophene and tetrahydrothiophene give the pentathiepin 10. X-Ray crystal structures are provided for the pentathiepins 1a and 1d, and possible reaction pathways are suggested for the extensive cascade reactions reported.

  在室温下，将亲核性杂环如吡咯和噻吩及其四氢衍生物与S2Cl2和DABCO在氯仿中反应，可以简单地一步合成融合的单和双五元硫杂环戊烷。N-甲基吡咯及其2-氯和2,5-二氯衍生物以及N-甲基吡咯烷均生成相同的二氯五元硫杂环戊烷1a。N-乙基、异丙基和叔丁基吡咯烷的行为类似；异丙基吡咯烷还生成了双五元硫杂环戊烷6，后者经历了一个有趣的重组变为对称的单五元硫杂环戊烷1c。N-甲基和乙基吲哚根据反应条件分别生成2,3-二氯衍生物8或五元硫杂环戊烷吲哚9。噻吩和四氢噻吩生成五元硫杂环戊烷10。提供了五元硫杂环戊烷1a和1d的X射线晶体结构，并为报道的大量级联反应提出了可能的反应途径。
• Investigation of the Pentathiepin Functionality as an Inhibitor of Feline Immunodeficiency Virus (FIV) via a Potential Zinc Ejection Mechanism, as a Model for HIV Infection
  作者：Christopher R. M. Asquith、Tuomo Laitinen、Lidia S. Konstantinova、Graham Tizzard、Antti Poso、Oleg A. Rakitin、Regina Hofmann‐Lehmann、Stephen T. Hilton

  DOI：10.1002/cmdc.201800718

  日期：2019.2.19

  A small diverse library of pentathiepin derivatives were prepared to evaluate their efficacy against the nucleocapsid protein function of the feline immunodeficiency virus (FIV) as a model for HIV, using an in vitro cell culture approach. This study led to the development of nanomolar active compounds with low toxicity.

  使用体外细胞培养方法，准备了一个小小的五肽衍生物衍生物文库，以评估其对抗猫免疫缺陷病毒（FIV）作为HIV模型的核衣壳蛋白功能的功效。这项研究导致了低毒性的纳摩尔活性化合物的开发。
• Synthesis and Identification of Pentathiepin-Based Inhibitors of Sporothrix brasiliensis
  作者：Christopher R. M. Asquith、Ana C. S. Machado、Luisa H. M. de Miranda、Lidia S. Konstantinova、Rodrigo Almeida-Paes、Oleg A. Rakitin、Sandro A. Pereira

  DOI：10.3390/antibiotics8040249

  日期：——

  Sporothrix brasiliensis is the causative agent of zoonotic sporotrichosis in Brazil and is currently referred to as the most virulent species among those of clinical importance within the genus. Sporotrichosis is an emergent disease that has come to the forefront over two decades with a recent hot spot of sporotrichosis infection emerging in the state of Rio de Janeiro. The source of these infections

  巴西Sporothrix brasiliensis是巴西人畜共患孢子菌病的病原体，目前被认为是该属中具有临床重要性的最强毒种。孢子丝虫病是一种新兴疾病，在过去的二十年中一直处于最前沿，最近在里约热内卢州出现了孢子丝虫病感染的热点地区。自1998年以来，仅在巴西里约热内卢就报告了4000多例此类感染的传染源。我们开发了一个稀有的pentathiepin环系统的重点文库，并确定了产生化合物21和22的有效替代模式。这些化合物比伊曲康唑更有效，伊曲康唑是目前治疗孢子体病的标准。