[(Azepan-1-ylcarbonothioyl)sulfanyl]acetic acid | 6499-13-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 英文名称: [(Azepan-1-ylcarbonothioyl)sulfanyl]acetic acid
• 英文别名: 2-(azepane-1-carbothioylsulfanyl)acetic acid
• CAS: 6499-13-4
• 化学式: C₉H₁₅NO₂S₂
• 分子量: 233.356
• InChiKey: QZRFQUHIFJKBSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(Azepan-1-ylcarbonothioyl)sulfanyl]acetic acid 在 一水合肼 作用下， 以 水 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  5-硝基噻吩-2-甲醛甲醛缩氨基脲衍生物的合成及体外抗原生动物活性。

  摘要：

  通过简单的方法制备了5-硝基噻吩-2-甲醛的几种硫半脲衍生物，其中N（4）-硫半脲部分被脂族，芳基和环状胺取代。在这些硫代半咔唑化合物中，化合物11显示出显着的抗阿米巴活性，而化合物3比参考药物具有更高的抗滴虫活性。

  DOI：

  10.1016/s0960-894x(02)00703-5
• 作为产物：
  描述：

  在 盐酸 、 水 作用下， 生成 [(Azepan-1-ylcarbonothioyl)sulfanyl]acetic acid
  参考文献：
  名称：

  Structure–activity relationships of mononuclear metal–thiosemicarbazone complexes endowed with potent antiplasmodial and antiamoebic activities

  摘要：

  A useful concept for the rational design of antiparasitic drug candidates is the complexation of bioactive ligands with transition metals. In view of this, an investigation was conducted into a new set of metal complexes as potential antiplasmodium and antiamoebic agents, in order to examine the importance of metallic atoms, as well as the kind of sphere of co-ordination, in these biological properties. Four functionalized furyl-thiosemicarbazones (NT1-4) treated with divalent metals (Cu, Co, Pt, and Pd) to form the mononuclear metallic complexes of formula [M(L)(2)Cl-2] or [M(L)Cl-2] were examined. The pharmacological characterization, including assays against Plasmodium falciparum and Entamoeba histolytica, cytotoxicity to mammalian cells, and interaction with pBR 322 plasmid DNA was performed. Structure-activity relationship data revealed that the metallic complexation plays an essential role in antiprotozoal activity, rather than the simple presence of the ligand or metal alone. Important steps towards identification of novel antiplasmodium (NT1Cu, IC50 of 4.6 mu M) and antiamoebic (NT2Pd, IC50 of 0.6 mu M) drug prototypes were achieved. Of particular relevance to this work, these prototypes were able to reduce the proliferation of these parasites at concentrations that are not cytotoxic to mammalian cells. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2010.07.039

文献信息

• Synthesis of a new series of dithiocarbamate-linked peptidomimetics and their application in Ugi reactions
  作者：Azim Ziyaei Halimehjani、Mohammad Amin Ranjbari、Hamed Pasha Zanussi

  DOI：10.1039/c3ra44552f

  日期：——

  Novel peptidomimetics containing dithiocarbamate groups were synthesized via the Ugi reaction. Also, dithiocarbamates of natural amino acids were prepared and were used successfully in Ugi reactions to prepare novel peptidomimetics bearing amino acid and dithiocarbamate groups in a single structure. In addition the prepared dithiocarbamates based on amino acids are converted to the corresponding amides

  通过Ugi反应合成了含有二硫代氨基甲酸酯基团的新型拟肽。此外，还制备了天然氨基酸的二硫代氨基甲酸酯，并将其成功用于Ugi反应中，以制备具有单一结构的氨基酸和二硫代氨基甲酸酯基团的新型拟肽。另外，将基于氨基酸制备的二硫代氨基甲酸酯转化为相应的酰胺。
• Synthesis, spectral studies and antiamoebic activity of new 1-N-substituted thiocarbamoyl-3-phenyl-2-pyrazolines
  作者：Mohammad Abid、Abdul Roouf Bhat、Fareeda Athar、Amir Azam

  DOI：10.1016/j.ejmech.2007.10.032

  日期：2009.1

  Thirty new pyrazoline derivatives were synthesized by cyclization of Mannich bases with thiosemicarbazides being substituted by different cyclic and aromatic amines. The structures of the compounds were elucidated by elemental analyses, UV, IR, H-1 and C-13 NMR and ESI-MS spectral data. The in vitro antiamoebic activity was evaluated against Entamoeba histolytica in comparison with metronidazole used as reference substance. Out of the 30 compounds screened for antiamoebic activity, 10 (5, 6, 15, 18, 25-30) were found to be better inhibitors of E. histolytica since they showed lesser IC50 values than metronidazole. The preliminary results indicated that the presence of 3-chloro or 3-bromo substituent on the phenyl ring at position 3 of the pyrazoline ring enhanced the antiamoebic activity as compared to unsubstituted phenyl ring. The study suggests that the preliminary activity of these compounds may further be explored for the development of new targets for amoebiasis. (C) 2007 Elsevier Masson SAS. All rights reserved.
• Synthesis and antiamoebic activity of 3,7-dimethyl-pyrazolo[3,4-e][1,2,4] triazin-4-yl thiosemicarbazide derivatives
  作者：Shailendra Singh、Kakul Husain、Fareeda Athar、Amir Azam

  DOI：10.1016/j.ejps.2005.02.014

  日期：2005.6

  A series of 3,7-dimethyl-pyrazolo[3,4-e] [ 1,2,4]triazin-4-yl thiosemicarbazide derivatives 3-22 were prepared and evaluated in vitro against HMI:IMSS strain of Entamoeba histolytica, to identify the compounds for antiamoebic activity. They exhibited antiamoebic activity in the range (IC50 = 0.81-7.31 mu M). The results were compared to the activity of known drug metronidazole. It is inferred from the in vitro studies that the compounds 10, 11. 17 and 18 were found to be significantly better inhibitors of E. histolytica since IC50 values in the mu M range elicited by these compounds are much lower than metronidazole. Besides, compounds 11 and 17 have shown the most promising antiamoebic activity (IC50 = 0.81 mu M of 11, IC50 = 0.84 mu M of 17 versus IC50 = 1.81 mu M of metronidazole). The study suggests the possibility of developing triazine analogues as potential drug candidates for antiamoebic activity. (c) 2005 Elsevier B.V. All rights reserved.