2,5-di(3-indolyl)thiophene | 74306-98-2

• 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: 2,5-di(3-indolyl)thiophene
• 英文别名: 2,5-bis(1H-indol-3-yl)thiophene；2,5-Bis(3-indolyl)thiophene；3-[5-(1H-indol-3-yl)thiophen-2-yl]-1H-indole
• CAS: 74306-98-2
• 化学式: C₂₀H₁₄N₂S
• 分子量: 314.411
• InChiKey: TYIOKRROCJBINW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,5-bis(1-(phenylsulfonyl)-1H-indol-3-yl)thiophene 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 生成 2,5-di(3-indolyl)thiophene
  参考文献：
  名称：

  Synthesis and antitumor properties of 2,5-bis(3′-indolyl)thiophenes: Analogues of marine alkaloid nortopsentin

  摘要：

  A series of 11 bis-indolylthiophenes of type 8-10 were obtained by cyclization of diketones 4 and 7 using Lawesson's reagent. Derivatives 8c, 9c, 9d, and 10c were selected to be evaluated in the full panel of about 60 human tumor cell lines derived from nine human cancer cell types and showed antiproliferative activity generally in the micromolar range. The most sensitive cell lines were: CCRF-CEM, MOLT-4, HL60 (TB), and RPMI-8226 of the leukemia subpanel, HT29 and HCC-2998 cell lines of the colon sub-panel, NCI-H522 of the non-small cell lung cancer sub-panel, LOX IMVI of the melanoma sub-panel, and UO-31 of the renal cancer sub-panel. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.065

文献信息

• Pseudo five-component synthesis of 2,5-di(hetero)arylthiophenes via a one-pot Sonogashira–Glaser cyclization sequence
  作者：Dominik Urselmann、Dragutin Antovic、Thomas J J Müller

  DOI：10.3762/bjoc.7.174

  日期：——

  and easily available, stable starting materials were used, resulting in a concise and highly efficient route for the synthesis of the title compounds. This novel pseudo five-component synthesis starting from iodo(hetero)arenes is particularly suitable as a direct access to well-defined thiophene oligomers, which are of peculiar interest in materials science.

  基于连续的一锅 Sonogashira-Glaser 偶联环化序列，合成了多种 2,5-二（杂）芳基噻吩，收率中等至良好。使用单一的 Pd/Cu 催化剂系统，无需进一步添加催化剂，并且使用容易获得、稳定的起始材料，从而为合成标题化合物提供了一条简洁高效的路线。这种从碘（杂）芳烃开始的新型伪五组分合成特别适合直接获取定义明确的噻吩低聚物，这在材料科学中具有特殊意义。
• One-Pot Synthesis of 2,5-Bis(3-indolyl)-3,4-dinitrothiophene, 3-(2-Chloro-3,4-dinitrothien-2-yl)indole and Related Congeners
  作者：Ismail I. Fasfous、Mustafa M. El-Abadelah、Salim S. Sabri

  DOI：10.2174/157017811799304124

  日期：2011.12.1

  Direct interaction of indolylzinc chloride with 2,5-dichloro-3,4-dinitrothiophene (4) produced 2,5-bis(indol-3- yl)-3,4-dinitrothiophene (5) together with 3-(5-chloro-3,4-dinitrothien-2-yl)indole (6). Interaction of the latter compound with 1-methylpiperazine gave 3-[4,5-di(4-methylpiperazin-1-yl)-3-nitrothien-2-yl]indole (7), as the expected SN-Ar (addition-elimination) di-substitution product, together with 3-[5-(4-methylpiperazin-1-yl)-3-nitrothien-2-yl]indole (8), a mono-substituted product. The formation of 8 probably proceeds via an anomalous pathway, related to cine-substitution, with departure of the nitro group at C-4. Compound 4 underwent SN-Ar substitution reaction with 1-methylpiperazine to give the respective 2,5-di-(4-methylpiperazin-1-yl)-2,4-dinitrothiophene (9).

  吲哚基氯化锌与 2,5-二氯-3,4-二硝基噻吩 (4) 直接作用，生成 2,5-双（吲哚-3-基）-3,4-二硝基噻吩 (5) 以及 3-（5-氯-3,4-二硝基噻吩-2-基）吲哚 (6)。后一种化合物与 1-甲基哌嗪作用后，得到了 3-[4,5-二（4-甲基哌嗪-1-基）-3-硝基噻吩-2-基]吲哚（7），这是一种预期的 SN-Ar（加成-消除）二取代产物，同时还得到了 3-[5-（4-甲基哌嗪-1-基）-3-硝基噻吩-2-基]吲哚（8），这是一种单取代产物。8 的形成可能是通过一种异常途径进行的，与 C-取代有关，硝基离开了 C-4 位。化合物 4 与 1-甲基哌嗪发生 SN-Ar 取代反应，得到相应的 2,5-二（4-甲基哌嗪-1-基）-2,4-二硝基噻吩（9）。
• Kamenskii, A. B.; Smushkevich, Yu. I.; Livshits, A. I., Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, # 4, p. 665 - 671
  作者：Kamenskii, A. B.、Smushkevich, Yu. I.、Livshits, A. I.、Suvorov, N. N.

  DOI：——

  日期：——
• KAMENSKIJ A. B.; SMUSHKEVICH YU. I.; LIVSHCHITS A. I.; CYBOPOB N. N., ZH. ORGAN. XIMII, 1980, 16, HO 4, 758-765
  作者：KAMENSKIJ A. B.、 SMUSHKEVICH YU. I.、 LIVSHCHITS A. I.、 CYBOPOB N. N.

  DOI：——

  日期：——
• Synthesis and antitumor properties of 2,5-bis(3′-indolyl)thiophenes: Analogues of marine alkaloid nortopsentin
  作者：Patrizia Diana、Anna Carbone、Paola Barraja、Alessandra Montalbano、Annamaria Martorana、Gaetano Dattolo、Ornella Gia、Lisa Dalla Via、Girolamo Cirrincione

  DOI：10.1016/j.bmcl.2007.01.065

  日期：2007.4

  A series of 11 bis-indolylthiophenes of type 8-10 were obtained by cyclization of diketones 4 and 7 using Lawesson's reagent. Derivatives 8c, 9c, 9d, and 10c were selected to be evaluated in the full panel of about 60 human tumor cell lines derived from nine human cancer cell types and showed antiproliferative activity generally in the micromolar range. The most sensitive cell lines were: CCRF-CEM, MOLT-4, HL60 (TB), and RPMI-8226 of the leukemia subpanel, HT29 and HCC-2998 cell lines of the colon sub-panel, NCI-H522 of the non-small cell lung cancer sub-panel, LOX IMVI of the melanoma sub-panel, and UO-31 of the renal cancer sub-panel. (c) 2007 Elsevier Ltd. All rights reserved.