4-N(phenyl)piperazino dithiocarbamate | 66962-18-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-N(phenyl)piperazino dithiocarbamate
• 英文别名: phenyl piperidine dithiocarbamate；Dithiokohlensaeure-(4-phenyl-piperazid)；4-phenyl-piperazine-1-carbodithioic acid；4-Phenylpiperazine-1-carbodithioic acid
• CAS: 66962-18-3
• 化学式: C₁₁H₁₄N₂S₂
• 分子量: 238.378
• InChiKey: IZXGXPRKFJRXRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  4-N(phenyl)piperazino dithiocarbamate 在 氢氧化钾 、 一水合肼 作用下， 以 乙醇 、 水 为溶剂， 反应 18.5h， 生成 [(4-Phenylpiperazine-1-carbothioyl)amino]carbamodithioic acid
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of Substituted Thiosemicarbazides and of 1,3,4-Thiadiazole or 1,2,4-Triazole Derivatives

  摘要：

  The synthesized series of new thiosemicarbazide derivatives (1, 6-10) in reactions with carbon disulphide produced, according to the reaction conditions, the dithioacids (4, 30) or the 5-substituted 1,3,4-thiadiazolo-2-thiol derivatives (2, 27). The dithioacids were cyclized, in the reaction with hydrazine, into the 4ami-no-1,2,4-triazolo-2-thiol derivatives (5, 31). One of these compounds (31) was transformed into the 1,2,4-triazolo-1,3,4-thiadiazine derivative (33). The compounds 6-9 were also exposed to the condensation with aldehydes. 4-phenylpiperazinocarbothiohydrazide (6) was exposed to the action of isothiocyanates, which gave the compounds 16-20, and these cyclized to the 1,3,4-thiadiazoloamino derivatives (21-23).The susceptibility of aerobic and anaerobic bacteria to some of the new derivatives were tested. The anaerobes were the most susceptible at concentrations in ranges less than 6.2 to 100 mu g/mL to derivative: 9 (64% were susceptible), 1, 13 (for 60%), and 7 (for 56%).

  DOI：

  10.1080/10426500500269851
• 作为产物：
  描述：

  二硫化碳 、 N-苯基哌嗪 以 乙腈 为溶剂， 生成 4-N(phenyl)piperazino dithiocarbamate
  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

• 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。
• Synthesis of novel <i>N</i>-(naphthalen-1-yl)propanamide derivatives and evaluation their antimicrobial activity
  作者：Asaf E. Evren、Leyla Yurttas、Meral Yılmaz-Cankilic

  DOI：10.1080/10426507.2019.1657428

  日期：2020.2.1

  -1-yl)propanamide (2c), N-(naphthalen-1-yl)-2-[(5-nitro-1H-benzimidazol-2-yl)thio]propanamide (2e) and 2-[(4-methyl-4H-1,2,4-triazol-3-yl)thio]-N-(naphthalen-1-yl)propanamide (2f) showed anti-gram-positive bacterial activity at the half potency of chloramphenicol. Only one compound, 2-(benzothiazol-2-ylthio)-N-(naphthalen-1-yl)propanamide (2b) displayed anti-gram-negative bacterial activity against

  摘要 合成了新的N-(naphthalen-1-yl)丙酰胺并研究了其抗菌活性。通过使 N-(萘-1-基)丙酰胺与一些 2-巯基芳基或二硫代氨基甲酸盐衍生物反应来获得最终化合物。它们的结构由 1H-NMR 和 13C-NMR 光谱以及 LC-MS/MS 光谱数据确定。研究了合成的化合物对 10 种细菌和 10 种真菌的抗菌活性。所有化合物都显示出显着的活性。尤其是化合物 2-[(5-甲基-1,3,4-噻二唑-2-基)硫基]-N-(萘-1-基)丙酰胺(2a)、2-(苯并噻唑-2-基硫基)- N-(萘-1-基)丙烯酰胺(2b)，2-[(1-甲基-1H-咪唑-2-基)硫代]-N-(萘-1-基)丙酰胺(2c)，N-(naphthalen-1-yl)-2-[(5-nitro-1H-benzimidazol-2-yl)thio]propanamide (2e) 在酮康唑的一半效力下对至少一种真菌表现出
• 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, spectroscopic characterization and anticancer potential studies of organoruthenium(II) arene dithiocarbamate complexes
  作者：Athandwe M. Paca、Saheed O. Benson、Amos A. Fatokun、Peter A. Ajibade

  DOI：10.1080/17415993.2023.2253343

  日期：2024.1.2

  Four organoruthenium(II) arene dithiocarbamate complexes: RuCl(piperidine dithiocarbamate)(p-cymene), C1; RuCl(1-phenylpiperazine dithiocarbamate)(p-cymene), C2, RuCl(ethylphenyl dithiocarbamate)(p...

  四种有机钌(II)芳烃二硫代氨基甲酸酯络合物：RuCl(哌啶二硫代氨基甲酸酯)(对伞花烃)，C1； RuCl(1-苯基哌嗪二硫代氨基甲酸酯)(对伞花烃), C2, RuCl(乙基苯基二硫代氨基甲酸酯)(p...
• 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.