S-methyl-3-(4-methoxybenzylidene)dithiocarbazate | 72815-30-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: S-methyl-3-(4-methoxybenzylidene)dithiocarbazate
• 英文别名: methyl 2-(4-methoxybenzylidene)hydrazinecarbodithioate；4-Methoxy-benzaldehyd-；(4-methoxy-benzylidene)-dithiocarbazic acid methyl ester；(4-Methoxy-benzyliden)-dithiocarbazidsaeure-methylester；Methyl 3-(4-methoxyphenylmethylene)dithiocarbazate；methyl N-[(4-methoxyphenyl)methylideneamino]carbamodithioate
• CAS: 72815-30-6
• 化学式: C₁₀H₁₂N₂OS₂
• 分子量: 240.35
• InChiKey: KMNHZUHNPYEANV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  91
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  S-methyl-3-(4-methoxybenzylidene)dithiocarbazate 在 potassium permanganate 、 溶剂黄146 作用下， 反应 2.0h， 生成 2-(4-methoxyphenyl)-5-methylsulfonyl-1,3,4-thiadiazole
  参考文献：
  名称：

  5-（取代苯基）的合成4-乙酰基-2-甲硫基Δ 2 -1,3,4-噻二唑类以及它们与氧化高锰酸钾

  摘要：

  醛甲硫基（硫代羰基）腙（2）与乙酸酐或乙酰氯反应，得到5-（取代苯基）4-乙酰基-2-甲硫基Δ 2 -1,3,4-噻二唑类（3）。在乙酸中用高锰酸钾（3）化合物的氧化配5-芳基-2-甲磺酰基-1,3,4-噻二唑（4），4-乙酰基-5-芳基- 2-甲基磺酰基Δ 2 -1,3- ，4-噻二唑类（5），和4-乙酰基-5-芳基- 2-甲基磺酰基Δ 2 -1,3,4-噻二唑啉1,1-二氧化物（6）。

  DOI：

  10.1039/p19830000967
• 作为产物：
  描述：

  肼基二硫代甲酸甲酯 、 4-甲氧基苯甲醛 在 硫酸 作用下， 以 甲醇 为溶剂， 生成 S-methyl-3-(4-methoxybenzylidene)dithiocarbazate
  参考文献：
  名称：

  新型缩硫脲衍生物的合成、抗菌和抗癌活性

  摘要：

  合成了对氨基苯甲酸 (PABA) 的硫缩氨基脲并测试了它们的抗菌和抗癌活性。发现异羟肟酸酯衍生物 4a-4l 比它们的酸对应物具有更好的抗微生物和抗癌活性。发现化合物4d对大肠杆菌、肺炎克雷伯菌、金黄色葡萄球菌、霍乱弧菌和枯草芽孢杆菌具有良好的抗菌活性，IC50值约为1 µM。化合物 4f 对白色念珠菌显示出有效的抗真菌活性 (IC50 = 1.29 µM)，化合物 4h 显示出有效的抗癌活性 (IC50 = 0.07 µM)。

  DOI：

  10.1002/ardp.201000201

文献信息

• 2-Acetylpyridine thiosemicarbazones. 1. A new class of potential antimalarial agents
  作者：Daniel L. Klayman、Joseph F. Bartosevich、T. Scott Griffin、Carl J. Mason、John P. Scovill

  DOI：10.1021/jm00193a020

  日期：1979.7

  Based on the antimalarial properties observed for 2-acetylpyridine 4-phenyl-3-thiosemicarbazone (1), an extensive series of related thiosemicarbazones was prepared and tested against Plasmodium berghei in mice. Screening results indicated that the presence of the 2-pyridylethylidene group was critical and that certain phenyl, benzyl, phenethyl, or cycloalkyl groups at N4 of the thiosemicarbazone moiety

  基于对2-乙酰基吡啶4-苯基-3-硫代半乳糖苷（1）观察到的抗疟疾特性，制备了一系列相关的硫代半胱氨酸并在小鼠中对柏氏疟原虫进行了测试。筛选结果表明2-吡啶基亚乙基的存在是关键的，并且在硫半脲部分的N 4处的某些苯基，苄基，苯乙基或环烷基也有助于抗疟活性。
• Synthesis, antimicrobial studies, and molecular docking of some new dihydro-1,3,4-thiadiazole and pyrazole derivatives derived from dithiocarbazates
  作者：Amr Hassan Moustafa、Doaa H. Ahmed、Mohamed T. M. El-Wassimy、Mamdouh F. A. Mohamed

  DOI：10.1080/00397911.2020.1843179

  日期：2021.2.16

  A series of 3-acetyl-2-aryl-5-methylthio-2,3-dihydro-1,3,4-thiadiazoles 3a–g, N- (4-acetyl-5-aryl-4,5-dihydro-1,3,4-thiadiazol-2-yl) acetamide derivatives 5a–e and spiro-compound 7 was prepared fro...

  一系列 3-乙酰-2-芳基-5-甲硫基-2,3-二氢-1,3,4-噻二唑 3a–g, N-(4-乙酰-5-芳基-4,5-二氢-1 ,3,4-噻二唑-2-基)乙酰胺衍生物 5a-e 和螺环化合物 7 是由...
• 1,3,4-Thia- and -selenadiazole and 1,2,4-triazolo[4,3-a]pyrimidine derivatives from hydrazonoyl halides
  作者：Nadia A. Abdel-Riheem、Nora M. Rateb、Ali A. Al-Atoom、Abdou O. Abdelhamid

  DOI：10.1002/hc.10156

  日期：——

  1,2,4-Triazolo[4,3-a]pyrimidines, thiadiazolines, selenadiazolines, and unsymmetrical azines were synthesized via reactions of a 4-isopropylbenzoyl bromide 4-nitrophenylhydrazone with each of potassium thiocyanate, potassium selenocyanate, ethyl 6-methyl-4-[4-(methylethyl)phenyl]-2-methylthio-3,4-dihydropyrimidine-5-carboxylate, and alkyl carbodithioate. © 2003 Wiley Periodicals, Inc. Heteroatom Chem

  1,2,4-三唑并[4,3-a]嘧啶、噻二唑啉、硒二唑啉和不对称吖嗪通过 4-异丙基苯甲酰溴 4-硝基苯腙与硫氰酸钾、硒氰酸钾、6-甲基乙基4-[4-(甲基乙基)苯基]-2-甲硫基-3,4-二氢嘧啶-5-羧酸酯和碳二硫代烷基酯。© 2003 Wiley Periodicals, Inc. 杂原子化学 14:421–426, 2003; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.10156
• Methyl-2-arylidene hydrazinecarbodithioates: synthesis and biological activity
  作者：Manojkumar Mahapatra、Umasankar Kulandaivelu、Philipp Saiko、Geraldine Graser、Thomas Szekeres、Graciela Andrei、Robert Snoeck、Jan Balzarini、Venkatesan Jayaprakash

  DOI：10.2478/s11696-013-0346-4

  日期：2013.1.1

  Methyl-2-arylidene hydrazine-carbodithioate has not been of particular interest to researchers even though its metal complexes are extensively reported on due to their biological activity. This study examined the cytostatic and antiviral activity of twelve methyl-2-arylidene hydrazinecarbodithioates reported by many researchers as intermediates for the synthesis of thiosemicarbazides and the preparation of their metal complexes. Compounds IIc, IIi, and IIl with tridentate ligand features were found to have the lowest IC50 value (6.5 μM, ≈ 1 μM, and 0.8 μM, respectively) against HL60 human promyelocytic leukemia cells. They were also most inhibitory to human embryonic lung (HEL) fibroblast proliferation (5.3 μM, 17 μM, and 2.6 μM). Compound IIc and IIl show antiviral activity against wild-type herpes simplex virus (HSV), varicella zoster virus (VZV), and acyclovirresistant HSV; however, these activities were observed at concentrations at which the compounds also markedly inhibit HL60 and HEL cell proliferation.

  摘要：甲基-2-芳基亚硫酰肼-卡巴二硫酸酯尽管其金属配合物因其生物活性而被广泛报道，但并未引起研究人员的特别关注。本研究考察了十二种甲基-2-芳基亚硫酰肼-卡巴二硫酸酯的细胞静止和抗病毒活性，这些化合物被许多研究人员报告为噻唑半脒的合成中间体和其金属配合物的制备。具有三齿配体特征的IIc、IIi和IIl化合物被发现对HL60人类前粒细胞白血病细胞具有最低的IC50值（分别为6.5μM、≈1μM和0.8μM）。它们对人类胚胎肺（HEL）成纤维细胞增殖抑制最强（分别为5.3μM、17μM和2.6μM）。化合物IIc和IIl对野生型单纯疱疹病毒（HSV）、带状疱疹病毒（VZV）和阿昔洛韦耐药HSV具有抗病毒活性；然而，这些活性在化合物显著抑制HL60和HEL细胞增殖的浓度下被观察到。
• A convenient route for the synthesis of new thiadiazoles
  作者：Abdelwahed SAYED、Yasser ZAKI、Emad AISH

  DOI：10.3906/kim-1505-13

  日期：——

  The present work describes the preparation of new thiadiazoles through a simple intramolecular reaction of mono- and bis-hydrazonoyl halides with methyl hydrogen phenyl carbonimidodithioate or methyl-2-arylidene hydrazinecarbodithioate. The synthetic method involves nucleophilic substitution followed by intramolecular cyclization reactions mediated by evolution of methanethiol. The structures of the title compounds were elucidated by elemental analyses, and FTIR, MS and NMR spectra.

  目前的工作描述了通过单亚肼基卤化物和双亚肼酰卤与甲基氢苯基碳酰亚胺二硫代酸酯或甲基-2-亚芳基肼碳二硫代酸酯的简单分子内反应制备新型噻二唑。该合成方法涉及亲核取代，然后是由甲硫醇的演化介导的分子内环化反应。通过元素分析、FTIR、MS 和 NMR 光谱阐明了标题化合物的结构。