4-benzyl-piperazine-1-carbodithioic acid | 46734-46-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-benzyl-piperazine-1-carbodithioic acid
• 英文别名: 4-Benzylpiperazine-1-carbodithioic acid
• CAS: 46734-46-7
• 化学式: C₁₂H₁₆N₂S₂
• 分子量: 252.404
• InChiKey: XBIUUXRZZVMQPK-UHFFFAOYSA-N

物化性质

• 沸点：
  347.2±52.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  39.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(bromomethyl)-2-phenyl-3H-quinazolin-4-one 、 4-benzyl-piperazine-1-carbodithioic acid 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (3,4-dihydro-4-oxo-2-phenylquinazolin-6-yl)methyl 4-benzylpiperazine-1-carbodithioate
  参考文献：
  名称：

  2-取代喹唑啉-4(3H)-酮哌嗪-1-碳二硫代衍生物的合成及细胞毒性筛选

  摘要：

  从 2-氨基-5-甲基苯甲酸开始，通过五步法合成了一系列新的 2-取代喹唑啉-4(3H)-酮的哌嗪-1-碳二硫代衍生物。通过 MTT 法测定所得化合物对 A-549（人肺癌）、HCT-8（人结肠癌）、HepG2（人肝癌）和 K562（人骨髓性白血病）细胞系的细胞毒性。报告了这些化合物的初步筛选结果。

  DOI：

  10.1002/ardp.200800148
• 作为产物：
  描述：

  二硫化碳 、 1-苄基哌嗪 以 乙腈 为溶剂， 生成 4-benzyl-piperazine-1-carbodithioic acid
  参考文献：
  名称：

  Dithiocarbamation of spiro-aziridine oxindoles: a facile access to C3-functionalised 3-thiooxindoles as apoptosis inducing agents

  摘要：

  已经通过直接对螺环-氮杂环氧吲哚进行二硫代氨基化，实现了对C3-官能化3-硫代氧吲哚的高效访问。已经研究了它们的诱导凋亡性能。

  DOI：

  10.1039/d1ob02102h

文献信息

• Development of benzene and benzothiazole-sulfonamide analogues as selective inhibitors of the tumor-associated carbonic anhydrase IX
  作者：Shoaib Manzoor、Andrea Angeli、Susi Zara、Simone Carradori、Md Ataur Rahman、Md Kausar Raza、Claudiu T. Supuran、Nasimul Hoda

  DOI：10.1016/j.ejmech.2022.114793

  日期：2022.12

  against CA I, II and IX, and weak inhibition against CA IV. Some of the derivatives displayed selective inhibition towards tumor-associated CA IX isoform, within the nanomolar range. These potent compounds were also screened for their selective toxicity to evaluate their in vitro anti-proliferative effects on Human Gingival Fibroblasts (HGFs) and breast adenocarcinoma cell line (MCF7). Lastly, molecular

  为了开发新的潜在抗肿瘤剂，已使用尾部方法开发了两个系列的苯和苯并噻唑磺酰胺衍生物，作为有效的人碳酸酐酶 (hCA, EC 4.2.1.1) 抑制剂。合成的化合物（XS-1至XS-22) 对 hCA 的生理相关异构体、细胞溶质 CA I 和 II、膜结合 CA IV 和肿瘤相关 CA IX 的抑制作用进行了测定。发现这两个系列的化合物对 CA I、II 和 IX 表现出低至中等纳摩尔范围的抑制作用，对 CA IV 表现出弱抑制作用。一些衍生物在纳摩尔范围内对肿瘤相关的 CA IX 异构体表现出选择性抑制。还筛选了这些有效化合物的选择性毒性，以评估它们对人牙龈成纤维细胞 (HGF) 和乳腺癌细胞系 (MCF7) 的体外抗增殖作用。最后，进行了分子对接研究，以解释那些有助于区分选定的人碳酸酐酶同种型的结构要求。
• Synthesis, antifungal activities and molecular docking studies of novel 2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl dithiocarbamates
  作者：Yan Zou、Shichong Yu、Renwu Li、Qingjie Zhao、Xiang Li、Maocheng Wu、Ting Huang、Xiaoxun Chai、Honggang Hu、Qiuye Wu

  DOI：10.1016/j.ejmech.2014.01.009

  日期：2014.3

  A series of 2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl dithiocarbamates as new analogs of fluconazole were synthesized and their antifungal activities were evaluated. Among these compounds, 2a-f and 3a-q exhibited higher activities than fluconazole against nearly all fungi tested except Aspergillus fumigatus. Noticeably, the in vitro biological activities of 2b, 3a, 3c, 3h-k, and 3o-q against Candida species were much better than those of fluconazole and ketoconazole. Also, 2a-d, 3a-d, 3e-f, 3h-k, 3p and 3q showed higher activities against A. fumi than fluconazole. Computational docking experiments indicated that the inhibition of CYP51 involved a coordination bond with iron of the heme group, the hydrophilic H-bonding region, the hydrophobic region, and the narrow hydrophobic cleft. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Synthesis and Cytotoxicity Screening of Piperazine-1-carbodithioate Derivatives of 2-Substituted Quinazolin-4(3<i>H</i>)-ones
  作者：Sheng-Li Cao、Yan-Wen Guo、Xian-Bo Wang、Mei Zhang、Yu-Ping Feng、Yu-Yang Jiang、Yue Wang、Qian Gao、Jian Ren

  DOI：10.1002/ardp.200800148

  日期：2009.3

  piperazine‐1‐carbodithioate derivatives of 2‐substituted quinazolin‐4(3H)‐ones were synthesized via a five‐steps procedure starting from 2‐amino‐5‐methylbenzoic acid. The cytotoxicity of the resulting compounds against A‐549 (human lung cancer), HCT‐8 (human colon cancer), HepG2 (human liver cancer), and K562 (human myelogenous leukaemia) cell lines was determined by the MTT assay. Preliminary screening results of

  从 2-氨基-5-甲基苯甲酸开始，通过五步法合成了一系列新的 2-取代喹唑啉-4(3H)-酮的哌嗪-1-碳二硫代衍生物。通过 MTT 法测定所得化合物对 A-549（人肺癌）、HCT-8（人结肠癌）、HepG2（人肝癌）和 K562（人骨髓性白血病）细胞系的细胞毒性。报告了这些化合物的初步筛选结果。
• Dithiocarbamation of spiro-aziridine oxindoles: a facile access to C3-functionalised 3-thiooxindoles as apoptosis inducing agents
  作者：Akash P. Sakla、Biswajit Panda、Kritika Laxmikeshav、Jay Prakash Soni、Sonal Bhandari、Chandraiah Godugu、Nagula Shankaraiah

  DOI：10.1039/d1ob02102h

  日期：——

  An efficient access to C3-functionalised 3-thiooxindoles has been accomplished via direct dithiocarbamation of spiro-aziridine oxindoles. Their apoptosis-inducing properties have been investigated.

  已经通过直接对螺环-氮杂环氧吲哚进行二硫代氨基化，实现了对C3-官能化3-硫代氧吲哚的高效访问。已经研究了它们的诱导凋亡性能。