3-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-indole | 82380-65-2

• 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: 3-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-indole
• 英文别名: 2-(1H-indol-3-yl)-5-methyl-1,3,4-oxadiazole
• CAS: 82380-65-2
• 化学式: C₁₁H₉N₃O
• mdl: MFCD12003905
• 分子量: 199.212
• InChiKey: UHWOXTBRTCBJEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  54.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-indole 以 formamide 为溶剂， 以58%的产率得到3-(5-methyl-1H-1,2,4-triazol-3-yl)-1H-indole
  参考文献：
  名称：

  Synthesis of di- and trisubstituted 1,2,4-triazoles containing indole fragments

  摘要：

  DOI：

  10.1007/bf00531658
• 作为产物：
  描述：

  吲哚-3-甲酸甲酯 在 一水合肼 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 14.0h， 生成 3-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-indole
  参考文献：
  名称：

  Synthesis and antifungal activity of 3-(1,3,4-oxadiazol-5-yl)-indoles and 3-(1,3,4-oxadiazol-5-yl)methyl-indoles

  摘要：

  On the basis of the principle of combination of active structural moieties, a modified and efficient synthetic method for three series of novel indole-based 1,3,4-oxadiazoles is described. Bioassays conducted at Syngenta showed that several of the synthesized compounds exhibit higher antifungal activity than pimprinine, the natural product which inspired this synthesis. Two main structural-alterations were found to broaden the spectrum of biological activity in most cases. Compounds 3g, 6c, 6e, 6h, 9d, 9e, 9h and 9m (Fig. 1) were identified as the most active on the biological assays, and will be studied further. (c) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.038

文献信息

• An efficient synthesis and biological study of novel indolyl-1,3,4-oxadiazoles as potent anticancer agents
  作者：Dalip Kumar、Swapna Sundaree、Emmanuel O. Johnson、Kavita Shah

  DOI：10.1016/j.bmcl.2009.03.172

  日期：2009.8

  A facile, convenient and high yielding synthesis of a series of novel 5-(3′-indolyl)-2-(substituted)-1,3,4-oxadiazoles from readily available starting materials has been described. The key step of this protocol is oxidative cyclization of N-acylhydrazones 1 using [bis(trifluoroacetoxy)iodo]benzene under solvent-free condition. The 5-(3′-indolyl)-2-(substituted)-1,3,4-oxadiazoles were screened for their

  已经描述了从容易获得的起始原料容易，方便且高产率地合成一系列新颖的5-（3'-吲哚基）-2-（取代的）-1,3,4-恶二唑。该协议的关键步骤是在无溶剂条件下使用[双（三氟乙酰氧基）碘]苯对N-酰基hydr 1进行氧化环化。筛选了5-（3'-吲哚基）-2-（取代）-1,3,4-恶二唑类化合物对各种人类癌细胞系的体外抗癌活性。化合物3C，3D和3J显示出强的细胞毒性（IC 50〜1μM）和选择性针对人肿瘤细胞株。
• Synthesis and functionalization of the 3-(1,3,4-oxadiazol-2-yl)-1h-indoles
  作者：S. B. Alyab’ev、D. V. Kravchenko、A. V. Ivashchenko

  DOI：10.1007/s10593-010-0418-0

  日期：2009.10

  A modified method is proposed for the preparative synthesis of 3-(1,3,4-oxadiazol-2-yl)-1H-indoles in high yield. We are the first to demonstrate the functionalization of this heterocyclic system by alkylation. In particular, syntheses are reported for [3-(1,3,4-oxadiazol-2-yl)-1H-indol-1-yl]acetic acids and their amide derivatives.
• Synthesis and properties of azoles and their derivatives. 33. Synthesis of 1,3,4-oxadiazoles that contain an indolyl group
  作者：V. I. Kelarev、G. A. Shvekhgeimer

  DOI：10.1007/bf00522123

  日期：1982.3
• KARAKHANOV, R. A.;KELAREV, V. I.;KOKOSOVA, A. S.;NASYROV, I. M.;KUSHETZOV+, PROC. 5TH CONF. APPL. CHEM. UNIT. OPER. AND PROCESS., BALATONFURED, 3-7 S+
  作者：KARAKHANOV, R. A.、KELAREV, V. I.、KOKOSOVA, A. S.、NASYROV, I. M.、KUSHETZOV+

  DOI：——

  日期：——
• MONGE, VEGA, A.;RABBANI, M. M.;FERNANDEZ-ALVAREZ, E., BOL. SOC. QUIM. PERU., 1983, 49, N 2, 120-130
  作者：MONGE, VEGA, A.、RABBANI, M. M.、FERNANDEZ-ALVAREZ, E.

  DOI：——

  日期：——