2-(naphthalen-2-ylmethylidene)hydrazinocarbothioamide | 24091-06-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(naphthalen-2-ylmethylidene)hydrazinocarbothioamide
• 英文别名: 2-((naphthalen-2-yl)methylidene)hydrazinecarbothioamide；2-Formyl-naphthalin-thiosemicarbazon；1-(naphthalen-2-ylmethylene)thiosemicarbazide；1-(naphthalene-2-ylmethylene)thiosemicarbazide；[2]naphthaldehyde-thiosemicarbazone；[2]Naphthaldehyd-thiosemicarbazon；(Naphthalen-2-ylmethylideneamino)thiourea
• CAS: 24091-06-3
• 化学式: C₁₂H₁₁N₃S
• mdl: MFCD00583369
• 分子量: 229.305
• InChiKey: YGAUDXIKISOSGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(naphthalen-2-ylmethylidene)hydrazinocarbothioamide 在 sodium acetate 、 potassium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 5.0h， 生成 (Z)-3-((benzyloxy)methyl)-2-(((E)-naphthalen-2-ylmethylene)hydrazono)thiazolidin-4-one
  参考文献：
  名称：

  Design and synthesis of thiazolylhydrazone derivatives as inhibitors of chitinolytic N-acetyl-β-d-hexosaminidase

  摘要：

  N-acetyl-beta-D-hexosaminidase (Hex) is potential target for pesticide design. Here, a series of thiazolylhydrazone derivatives were designed, synthesized and evaluated as competitive inhibitors of OfHex1, a Hex from the agricultural pest Ostrinia furnacalis. The derivative 3k, with a (benzyloxy) methyl group at the N3 atom, demonstrated greater potency with a K-i of 10.2 mu M. Molecular docking analysis indicated that the (benzyloxy) methyl group of 3k was bound to a previously unexplored pocket formed by Loop478-496. Then further optimization around naphthalene ring led to find the more potency substituent phenyl. The derivative 7, with phenoxyethyl group at R-1 and a phenyl group at R-2, demonstrated an augmented potency with a K-i of 2.1 mu M. Molecular docking analysis indicated that 7 was bound to the active pocket of OfHex1 more favorably than 3k. This work suggests a novel scaffold for developing specific Hex inhibitors.

  DOI：

  10.1016/j.bmc.2018.09.014
• 作为产物：
  描述：

  2-萘甲醛 生成 2-(naphthalen-2-ylmethylidene)hydrazinocarbothioamide
  参考文献：
  名称：

  Popovici, Annales de Chimie (Cachan, France), 1932, vol. <10> 18, p. 183,228

  摘要：

  DOI：

文献信息

• Design and Efficient Synthesis of Novel 4,5-Dimethylthiazole-Hydrazone Derivatives and their Anticancer Activity
  作者：Asaf Evrim Evren、Leyla Yurttaş、Büşra Ekselli、Onur Aksoy、Gülşen Akalin-Çiftçi

  DOI：10.2174/1570180817999201022192937

  日期：2021.4

  this purpose, our research group designed and synthesized novel 4,5-dimethyl thiazole-hydrazone derivatives which were tested against cancer and normal cell lines to understand the structureactivity relationship (SAR). Methods: The lead compounds were obtained by reacting 2-(substituted aryl-2-ylmethylene) hydrazin-1-carbothioamide with 3-chloro-2-butanone derivatives. The structural elucidation of the

  背景：最近，研究人员已警告各种癌症类型的死亡率增加。而且，由于晚期或错误的诊断和/或不足的治疗方法，肺腺癌和神经胶质瘤类型是世界健康的迫在眉睫的问题。为此，我们的研究小组设计并合成了新颖的4,5-二甲基噻唑-衍生物，并对其进行了抗癌和正常细胞株测试，以了解其结构活性关系（SAR）。方法：通过使2-（取代的芳基-2-基亚甲基）肼-1-碳硫酰胺与3-氯-2-丁酮衍生物反应制得先导化合物。通过1 H-NMR，13 C-NMR和LC / MS-IT-TOF光谱和元素分析进行​​化合物的结构阐明。体外测试了合成的化合物对A549人肺腺癌和C6大鼠神经胶质瘤细胞的抗癌活性，并研究了诱导细胞死亡的途径。此外，完成了对活性化合物的对接研究，以了解SAR。
• The synthesis and antiparasitic activity of aryl- and ferrocenyl-derived thiosemicarbazone ruthenium(ii)–arene complexes
  作者：Muneebah Adams、Yiqun Li、Heena Khot、Carmen De Kock、Peter J. Smith、Kirkwood Land、Kelly Chibale、Gregory S. Smith

  DOI：10.1039/c3dt32740j

  日期：——

  the imine nitrogen and the thione sulfur atoms. The thiosemicarbazone ligands, as well as their metal complexes, were characterized by NMR, IR spectroscopy and ESI+-mass spectrometry. The molecular structure of the mononuclear ruthenium(II)–arene thiosemicarbazone complex (6) was determined by single-crystal X-ray diffraction analysis. The ruthenium(II)–arene thiosemicarbazone complexes were further

  通过一般的席夫碱缩合反应，以中等收率合成了一系列芳基官能化和二茂铁基单硫代半碳氮酮化合物（L1-L4）。硫代半脲酮（TSC）配体与钌二聚体[Ru（Ar）（μ-Cl）Cl] 2（Ar =苯；对甲基异丙基苯）反应生成一系列阳离子单核钌（II）-芳烃一般类型[Ru（Cl）（TSC）（Ar）] Cl（1–8）。硫半脲配体起双齿螯合配体的作用，可与钌（II）离子通过亚胺氮和硫酮硫原子。通过NMR，IR光谱和ESI + -质谱法表征了硫半脲配体及其金属配合物。通过单晶X射线衍射分析确定了单核钌（II）-芳烃硫代半碳杂zone配合物（6）的分子结构。进一步评估了钌（II）-芳烃硫半碳杂zone配合物对恶性疟原虫氯喹敏感性（NF54）和氯喹抗性（Dd2）菌株以及阴道毛滴虫G3菌株的体外抗寄生虫活性。
• Facile and convenient synthesis of 2,4-disubstituted and 2,3,4-trisubstituted 1,3-thiazoles
  作者：Alaa A. Hassan、Shaaban K. Mohamed、Nasr K. Mohamed、Kamal M.A. El-Shaieb、Ahmed T. Abdel-Aziz、Joel T. Mague、Mehmet Akkurt

  DOI：10.1080/17415993.2015.1114621

  日期：2016.3.3

  ABSTRACT An efficient route for the synthesis of (E)-2-(2-(2-nitrobenzylidene)-hydrazinyl)-4-phenylthiazol-3-ium bromide, (E)-2-(2(substituted benzylidene)hydrazinyl)-4-phenylthiazoles and (E)-4-(4-bromophenyl)-2-(cycloalkylidenehydrazono)-3-phenyl-2,3-dihydrothiazoles by reaction of 1-aryl-2-bromoethanones with 2-(1-substituted methylidene)hydrazinecarbothioamides and cycloalkylidene-N-phenyl-hyd

  摘要 一种合成 (E)-2-(2-(2-nitrobenzylidene)-hydrazinyl)-4-phenylthiazol-3-ium bromide, (E)-2-(2(取代的苯亚甲基)hydrazinyl)-的有效途径4-苯基噻唑和 (E)-4-(4-溴苯基)-2-(亚环烷基肼基)-3-苯基-2,3-二氢噻唑通过 1-芳基-2-溴乙酮与 2-(1-取代的亚甲基)反应肼碳硫酰胺和亚环烷基-N-苯基-肼碳硫酰胺。产物的结构已通过红外、核磁共振、质谱和单晶X射线分析确定。图形概要
• Synthesis and biological evaluation of thiazole and thiadiazole derivatives as potential anticancer agents
  作者：Sedanur Ekrek、Sevil Şenkardeş、Ömer Erdoğan、Özge Çevik

  DOI：10.1080/10426507.2022.2136665

  日期：2023.3.4

  the products were evaluated by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay against Hela cervical cancer, MCF-7 breast carcinoma and HT-29 colorectal cancer cell lines. Thiazole based compounds 2a, 2b, 2f and 2i, bearing 4-bromothiophen-2-yl, naphthalen-2-yl, 2,5-difluorophenyl and 4-(trifluoromethoxy)phenyl moieties, respectively; also N-(4-acetyl-5-(naphthalen-2-yl)-4,5-dihydro-1

  摘要 一系列新的 4-methyl-2-2-[(aryl)methylidene]hydrazinyl}-1,3-thiazole (2a-i) , N -(4-acetyl-5-aryl)4,5-dihydro- 1,3,4-噻二唑-2-基)乙酰胺(3a-b)和N -(5-(4-(取代苯基)-1,3,4-噻二唑-2-基)乙酰胺(3c-i)由 2-((aryl)methylene)hydrazine-1-carbothioamides (1a-i)和乙酸酐或氯丙酮反应合成。产物的细胞毒活性通过 MTT（3-（4,5-二甲基噻唑 - 2-yl)-2,5-diphenyltetrazolium bromide) assay against Hela cervical cancer, MCF-7 breast carcinoma and HT-29 colorectal cancer lines
• Refinement of arylthiosemicarbazone pharmacophore in inhibition of mushroom tyrosinase
  作者：Wei Yi、Carole Dubois、Samir Yahiaoui、Romain Haudecoeur、Catherine Belle、Huacan Song、Renaud Hardré、Marius Réglier、Ahcène Boumendjel

  DOI：10.1016/j.ejmech.2011.07.003

  日期：2011.9

  Melanin play a major role in human skin protection and their biosynthesis is vital. Due to their color, they contribute to the skin pigmentation. Tyrosinase is a key enzyme involved in the first stage of melanin biosynthesis, it catalyzes the transformation of tyrosine into L-dopaquinone. The aim of the present study was to study molecules able to inhibit tyrosinase to be used in treating depigmentation-related disorders. In this study, we targeted arylthiosemicarbazone analogs with the aim to contribute to the identification of the optimal aryl ring to be linked to the thiosemicarbazone moiety. The biological activity was evaluated on commercial mushroom tyrosinase which was purified prior use. The results demonstrated that several of our compounds (1a-h, 1j, 1r and 5) had more potent inhibitory activities than kojic acid which was used as the reference inhibitor. (C) 2011 Elsevier Masson SAS. All rights reserved.