N-[2-(2-cyanomethyl-6-methoxy-1,3,4-thiadiazolo[3,2-a]indol-4-yl)ethyl]acetamide | 639784-98-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-[2-(2-cyanomethyl-6-methoxy-1,3,4-thiadiazolo[3,2-a]indol-4-yl)ethyl]acetamide
• 英文别名: N-(2-(2-(cyanomethyl)-7-methoxy-[1,3,4]thiadiazolo[3,2-a]indol-9-yl)ethyl)acetamide；N-[2-[2-(cyanomethyl)-6-methoxy-[1,3,4]thiadiazolo[3,2-a]indol-4-yl]ethyl]acetamide
• CAS: 639784-98-8
• 化学式: C₁₆H₁₆N₄O₂S
• 分子量: 328.395
• InChiKey: WBSMMFFFARHJCY-UHFFFAOYSA-N

物化性质

• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[2-(2-cyanomethyl-6-methoxy-1,3,4-thiadiazolo[3,2-a]indol-4-yl)ethyl]acetamide 在 哌啶 、 potassium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 N-(2-(2-(cyano(4-oxo-3-phenylthiazolidin-2-ylidene)methyl)-7-methoxy-[1,3,4]thiadiazolo[3,2-a]indol-9-yl)ethyl)acetamide
  参考文献：
  名称：

  Novel Melatonin Derivatives: Synthesis, Anticancer Evaluations and Molecular-Docking Study

  摘要：

  DOI：

  10.21608/ejchem.2020.49430.3016
• 作为产物：
  描述：

  褪黑素 、 丙二腈 在 sulfur 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以69%的产率得到N-[2-(2-cyanomethyl-6-methoxy-1,3,4-thiadiazolo[3,2-a]indol-4-yl)ethyl]acetamide
  参考文献：
  名称：

  Doss; Mohareb, Rafat M.; Elmegeed, Pharmazie, 2003, vol. 58, # 9, p. 607 - 613

  摘要：

  DOI：

文献信息

• Potent neuroprotective role of novel melatonin derivatives for management of central neuropathy induced by acrylamide in rats
  作者：Hanaa H. Ahmed、Gamal A. Elmegeed、El-Sayed M. El-Sayed、Mervat M. Abd-Elhalim、Wafaa Gh. Shousha、Reham W. Shafic

  DOI：10.1016/j.ejmech.2010.09.017

  日期：2010.11

  Acrylamide (ACR) has been shown to be a neurotoxic agent for both laboratory animals and human. The present study aimed at synthesizing new functionalized melatonin derivatives bearing promising heterocyclic moiety that could be expected to have protective effect against ACR-induced neurotoxicity in adult female rats. The novel melatonin derivatives 4, 6, 7 and 11 were synthesized and their chemical structures were confirmed by studying their analytical and spectral data. The administration of ACR [i.p., 50 mg kg(-1) body weight (b. wt.)] alone resulted in significant increase in brain malondialdehyde level (MDA) and lactate dehydrogenase (LDH) activity whereas it caused significant decrease in brain monoamines levels and antioxidant enzymes activity. Treatment with melatonin derivatives 4, 6, 7 and 11 (i.p., 50 mg kg(-1) b. wt) prior to ACR produced significant decrease in brain MDA level and LDH activity with concomitant significant increase in brain monoamines and antioxidant enzymes activity. It could be concluded that the new synthesized melatonin derivatives exhibited promising protective activity against ACR-induced neurotoxicity. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Synthesis and in vivo anti-mutagenic activity of novel melatonin derivatives
  作者：Gamal A. Elmegeed、Wagdy K.B. Khalil、Amira Abdel Raouf、Mervat M. Abdelhalim

  DOI：10.1016/j.ejmech.2007.06.003

  日期：2008.4

  Extensive literature suggests that melatonin play a role against the degenerative effect of central neurotoxins by its acting as free radical scavenger. This study aimed at evaluation of the anti-mutagenic activity of novel synthesized indole derivatives 2, 4a, and 8 in albino male mice in comparison with the parent melatonin. Efficacy of melatonin and its derivatives to influence cyclophosphamide (CP)-induced genotoxicity was tested using micronuclei (MN) formation in the bone marrow cells and determination of DNA, RNA and protein levels as well as cholinesterase and peroxidase activities in several organs of male mice. Following intragastrical injection of melatonin or one of its derivatives daily for 1 week, CP was given intraperitoneally, i.p., as a single dose of 25 mg/kg BW. Pyridazin-4-yl thiadiazoloindole derivative 8, diaminothiophen-5-yi thiadiazoloindole derivative 4a and melatonin were significantly able to reduce the number of micronucleated polychromatic erythrocytes (MnPCEs) in the bone marrow cells induced by CP (P < 0.0001, P < 0.001, P < 0.01, respectively). However, reduction of MN formation in the bone marrow cells was not significant when thiadiazoloindole derivative 2 was administered (P = 0. 14). Examination of the protective effect of melatonin and its derivatives on the levels of DNA, RNA and protein as well as enzyme activities showed that compound 8 had the ability to inhibit the clastogenic effect of CP in several organs of male mice. These findings suggest that compounds 4a, 8 and melatonin were able to reduce the mutagenicity effect of CP in male mice. The ability of compounds 4a, 8 and melatonin to reduce CP-related genotoxicity is possibly attributed to their antioxidant activity. (c) 2007 Elsevier Masson SAS. All rights reserved.
• Doss; Mohareb, Rafat M.; Elmegeed, Pharmazie, 2003, vol. 58, # 9, p. 607 - 613
  作者：Doss、Mohareb, Rafat M.、Elmegeed、Luoca

  DOI：——

  日期：——
• Novel Melatonin Derivatives: Synthesis, Anticancer Evaluations and Molecular-Docking Study
  作者：Mahmoud Alsayed、Dina El-Kady、mohamed tantawy、Mervat AbdElhalim、Samia Elazabawy、Amira Abdallah、Gamal Elmegeed

  DOI：10.21608/ejchem.2020.49430.3016

  日期：2020.12.21