2-(benzo[d][1,3]dioxol-5-ylmethylene)-N-phenylhydrazinecarbothioamide | 83796-44-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-(benzo[d][1,3]dioxol-5-ylmethylene)-N-phenylhydrazinecarbothioamide
• 英文别名: PhpTSC；pPhTSC；benzo[1,3]dioxol-5-carbaldehyde 4-phenyl-thiosemicarbazone；(C7H5O2)CHN2HC(S)NHPh；Piperonal-(4-phenyl-thiosemicarbazon)；3,4-Methylendioxy-benzaldehyd-(4-phenyl-thiosemicarbazon)；1-(1,3-Benzodioxol-5-ylmethylideneamino)-3-phenylthiourea
• CAS: 83796-44-5
• 化学式: C₁₅H₁₃N₃O₂S
• 分子量: 299.353
• InChiKey: VPVHSSHLCMHCBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  87
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(benzo[d][1,3]dioxol-5-ylmethylene)-N-phenylhydrazinecarbothioamide 、 2-溴丙酸 在 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 生成 benzo[1,3]dioxole-5-carbaldehyde (5-methyl-4-oxo-3-phenyl-thiazolidin-2-ylidene)-hydrazone
  参考文献：
  名称：

  Shah,I.D.; Trivedi,J.P., Journal of the Indian Chemical Society, 1963, vol. 40, p. 889 - 893

  摘要：

  DOI：
• 作为产物：
  描述：

  胡椒醇 在 manganese(IV) oxide 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-(benzo[d][1,3]dioxol-5-ylmethylene)-N-phenylhydrazinecarbothioamide
  参考文献：
  名称：

  作为潜在细胞毒剂和抗寄生虫剂的苯并二恶唑衍生物的合成、热行为和生物学评价

  摘要：

  已知苯并二恶唑衍生物具有广泛的活性，例如。除了合成衍生物外，具有苯并二恶唑亚基的天然产物，如胡椒碱，通过诱导细胞凋亡和抗寄生虫活性显示出潜在的抗肿瘤活性。因此，含有苯并二恶唑亚基的化合物具有广谱活性，并提高了对治疗创新的期望。通过常规光谱方法（1 H NMR 和13C NMR），可以观察到它们都满足结构表征的先决条件。这些信息通过与质谱仪耦合的热解表征得到证实，因为所有化合物都呈现出具有各自质量的特征片段。除了通过TG、DSC对NW-11衍生物进行热分析，并获得衍生物的降解动力学。至于抗增殖活性，可以得出结论，在所有测试的苯并吲哚酚衍生物中，可以指出 NW-03 在抗肿瘤活性研究中很有前途。而对于抗寄生虫活性的结果，可以选择衍生物 NW-02 和 NW-09 作为潜在的杀锥虫药。用于对抗利什曼原虫的活动，除了化合物 NW-2 和 NW-15 之外，化合物 NW-14 本身也是有前途的化合物

  DOI：

  10.1007/s00044-023-03047-5

文献信息

• Synthesis and characterization of mixed-ligand diimine-piperonal thiosemicarbazone complexes of ruthenium(II): Biophysical investigations and biological evaluation as anticancer and antibacterial agents
  作者：Floyd A. Beckford、Jeffrey Thessing、Michael Shaloski、P. Canisius Mbarushimana、Alyssa Brock、Jacob Didion、Jason Woods、Antonio Gonzalez-Sarrías、Navindra P. Seeram

  DOI：10.1016/j.molstruc.2011.02.029

  日期：2011.4

  We have used a novel microwave-assisted method developed in our laboratories to synthesize a series of ruthenium-thiosemicarbazone complexes. The new thiosemicarbazone ligands are derived from benzo[d][1,3]dioxole-5-carbaldehyde (piperonal) and the complexes are formulated as [(diimine)(2) Ru(TSC)](PF6)(2) (where the TSC is the bidentate thiosemicarbazone ligand). The diimine in the complexes is either 2,2'-bipyridine or 1,10-phenanthroline. The complexes have been characterized by spectroscopic means (NMR, IR and UV-Vis) as well as by elemental analysis. We have studied the biophysical characteristics of the complexes by investigating their anti-oxidant ability as well as their ability to disrupt the function of the human topoisomerase ll enzyme. The complexes are moderately strong binders of DNA with binding constants of 10(4) M-1. They are also strong binders of human serum albumin having binding constants on the order of 10(4) M-1. The complexes show good in vitro anticancer activity against human colon cancer cells, Caco-2 and HCT-116 and indeed show some cytotoxic selectivity for cancer cells. The IC50 values range from 7 to 159 mu M (after 72 h drug incubation). They also have antibacterial activity against Gram-positive strains of pathogenic bacteria with IC50 values as low as 10 mu M: little activity was seen against Gram-negative strains. It has been established that all the compounds are catalytic inhibitors of human topoisomerase II. (C) 2011 Elsevier B.V. All rights reserved.
• One-pot and catalyst-free synthesis of thiosemicarbazones via multicomponent coupling reactions
  作者：Silvio Cunha、Tiago Lima da Silva

  DOI：10.1016/j.tetlet.2009.02.134

  日期：2009.5

  A novel and efficient procedure for the synthesis of thiosemicarbazones has been achieved via a multi-component and catalyst-free reaction of phenyl or p-chlorophenyl isothiocyanate, hydrazine, and aldehydes or ketones. The method afforded 20 thiosemicarbazones in good yields and short reaction time. (c) 2009 Elsevier Ltd. All rights reserved.
• Tisler, Zeitschrift fur Analytische Chemie, 1956, vol. 149, p. 164,165
  作者：Tisler

  DOI：——

  日期：——
• Anticancer activity and biophysical reactivity of copper complexes of 2-(benzo[d][1,3]dioxol-5-ylmethylene)-N-alkylhydrazinecarbothioamides
  作者：Floyd A. Beckford、Jeffrey Thessing、Alyssa Stott、Alvin A. Holder、Oleg G. Poluektov、Liya Li、Navindra P. Seeram

  DOI：10.1016/j.inoche.2011.10.032

  日期：2012.1

  A series of copper complexes were synthesized from benzo[d][1,3]dioxole-5-carbaldehyde (piperonal) thiosemicarbazones (RHpTSC where R = H, CH3, C2H5 or C6H5 (Ph)). The complexes show interesting variations in geometry depending on the thiosemicarbazone; a dinuclear complex [Cu(HpTSC)Cl]2, a mononuclear complex [Cu(RHpTSC)2Cl2] (R = CH3 or C2H5) and another mononuclear complex [Cu(PhHpTSC)(PhpTSC)Cl] was generated. The complexes bind in a moderately strong fashion to DNA with binding constants on the order of 10(4)M(-1). They are also strong binders of human serum albumin with binding constants near 10(4) M-1. The complexes show good in vitro cytotoxic profiles against two human colon cancer cell lines (HT-116 and HT29) and two human breast cancer cell lines (MCF-7 and MDA-MB-231) with IC50 values in the low millimolar concentration range. (C) 2011 Elsevier B.V. All rights reserved.
• Shah,I.D.; Trivedi,J.P., Journal of the Indian Chemical Society, 1963, vol. 40, p. 889 - 893
  作者：Shah,I.D.、Trivedi,J.P.

  DOI：——

  日期：——