6-ethyl-6H-[1,2,3,4,5]pentathiepino[6,7-b]indole

• 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-ethyl-6H-[1,2,3,4,5]pentathiepino[6,7-b]indole
• 英文别名: 6-Ethylpentathiepino[6,7-b]indole
• 化学式: C₁₀H₉NS₅
• 分子量: 303.518
• InChiKey: BGPWSZRIEXMBMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-乙基吲哚 在 二氯化二硫 作用下， 以 氯仿 为溶剂， 反应 48.0h， 以72%的产率得到6-ethyl-6H-[1,2,3,4,5]pentathiepino[6,7-b]indole
  参考文献：
  名称：

  通过潜在的锌喷射机制研究五肽作为猫免疫缺陷病毒（FIV）抑制剂的功能，作为HIV感染的模型

  摘要：

  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。

  DOI：

  10.1002/cmdc.201800718

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。
• 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。
• Regioselective synthesis of pentathiepino-fused pyrroles and indoles
  作者：Lidia S. Konstantinova、Oleg A. Rakitin、Charles W. Rees、Stanislav A. Amelichev

  DOI：10.1070/mc2004v014n03abeh001912

  日期：2004.1

  Treatment of simple pyrroles, pyrrolidines and indoles with S2Cl2 and Dabco in chloroform at room temperature gives their fused pentathiepino derivatives 4, 6 and 8 in extensive cascade reactions; the reaction profile is changed and the regioselectivity enhanced when the S2Cl2 and Dabco are premixed and equilibrated before the heterocycle is added.
• 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。