N',2-di-(benzylidene)hydrazine-1-carbothiohydrazide

• 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: N',2-di-(benzylidene)hydrazine-1-carbothiohydrazide
• 英文别名: Dibenzylidenethiocarbohydrazide；1,3-bis(benzylideneamino)thiourea
• 化学式: C₁₅H₁₄N₄S
• 分子量: 282.369
• InChiKey: QYIDDDFCXHCQEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N',2-di-(benzylidene)hydrazine-1-carbothiohydrazide 在 盐酸 、 乙醇 、 三氯化铁 作用下， 生成 (5-苯基-1,3,4-噻二唑-2-基)肼
  参考文献：
  名称：

  Sandstroem, Arkiv foer Kemi, 1956, vol. 9, p. 255,267

  摘要：

  DOI：
• 作为产物：
  描述：

  benzaldehyde thiocarbohydrazone 生成 N',2-di-(benzylidene)hydrazine-1-carbothiohydrazide
  参考文献：
  名称：

  Sandstroem,J., Acta Chemica Scandinavica (1947), 1960, vol. 14, p. 1037 - 1042

  摘要：

  DOI：

文献信息

• Synthesis of Thiocarbohydrazones and Evaluation of their in vitro Antileishmanial Activity
  作者：Munira T. Muhammad、Nida Ghouri、Khalid M. Khan、Arshia、Muhammad I. Choudhary、Shahnaz Perveen

  DOI：10.2174/1573406414666180115094630

  日期：2018.10.3

  Background: Leishmaniasis is a protozoan parasitic vector-borne disease which is endemic in 88 tropical countries. Infected sandfly is the main vector of this disease, while there are several other vectors, parasites, and reservoirs involved in the transmission of this disease. Leishmania donovani, L. infantum, and L. chagasi are common disease causing species, transmitted through sandflies. Leishmaniasis is a neglected tropical disease with broad spectrum of clinical manifestations. Cutaneous leishmaniasis is prevalent in many countries, including Pakistan. Methods: Thiocarbohydrazones (1-20) were synthesized through one pot method by refluxing thiocarbahydrazide with different substituted benzaldehydes in ethanol in the presence of acetic acid as a catalyst. These synthetic compounds were evaluated for their potential antileishmanial activity in vitro against Leishmania major promastigotes. Results: Compounds 5-8, 11, 14, 16, 17, 19 and 20 were reported earlier, while compounds 2-4, 9, 10, 12, 13 and 15 were identified as were derivatives. Compounds 1-20 demonstrated antileishmanial activities with IC50 values between 1.63 ± 0.05 - 64.82 ± 0.17 µM, as compared to the standard drug pentamidine (IC50 = 5.09 ± 0.04 µM). Compounds 2 (IC50 = 1.63 ± 0.05 µM), 11 (IC50 = 2.33 ± 0.01 µM), 4 (IC50 = 11.03 ± 0.20 µM), and 10 (IC50 = 11.63 ± 0.06 µM) displayed comparable antileishmanial activities to the standard drug pentamidine. However, compounds 13, 15-17, and 20 with IC50 values 36.95 ± 0.025, 64.82 ± 0.17, 64.27 ± 0.38, 62.34 ± 0.38, and 40.47 ± 0.05 µM, respectively, showed a moderate antileishmanial activity. In contrast, compounds 1, 3, 5-9, 12, 14, 18, and 19 demonstrated less than 50% growth inhibition of promestigotes of L. major, and thus considered as inactive. Conclusion: In thiocarbohydrazone derivatives, different substituents at aryl part may be responsible for a varying degree of antileishmanial activity in vitro. Consequently, these compounds might have a potential for further studies as a new class of antileishmanial agents.

  背景：利什曼病是一种原生动物寄生虫病媒传染病，在 88 个热带国家流行。受感染的沙蝇是这种疾病的主要传播媒介，同时还有其他几种传播媒介、寄生虫和储库参与这种疾病的传播。 唐氏利什曼原虫、婴儿利什曼原虫和查加斯利什曼原虫是常见的致病物种，通过沙蝇传播。利什曼病是一种被忽视的热带疾病，具有广泛的临床表现。皮肤利什曼病在包括巴基斯坦在内的许多国家都很流行。 方法：在乙酸作为催化剂的存在下，通过一锅法将硫代酰肼与不同取代的苯甲醛在乙醇中回流合成了硫代酰肼（1-20）。结果：化合物 5-8、11、14、16、17、19 和 20 早先已有报道，而化合物 2-4、9、10、12、13 和 15 则被鉴定为衍生物。与标准药物喷他脒（IC50 = 5.09 ± 0.04 µM）相比，化合物 1-20 具有抗利什曼病活性，IC50 值介于 1.63 ± 0.05 - 64.82 ± 0.17 µM。化合物 2（IC50 = 1.63 ± 0.05 µM）、11（IC50 = 2.33 ± 0.01 µM）、4（IC50 = 11.03 ± 0.20 µM）和 10（IC50 = 11.63 ± 0.06 µM）显示出与标准药物喷他脒相当的抗利什曼活性。然而，IC50 值分别为 36.95 ± 0.025、64.82 ± 0.17、64.27 ± 0.38、62.34 ± 0.38 和 40.47 ± 0.05 µM 的化合物 13、15-17 和 20 显示出中等程度的抗利什曼病活性。结论：在硫代羧腙衍生物中，芳基部分的不同取代基可能是体外抗利什曼活性不同的原因。因此，这些化合物可能有潜力作为一类新的抗利什曼病药进行进一步研究。
• A Hydrazine- and Phosgene-Free Synthesis of Tetrazinanones, Precursors to 1,5-Dialkyl-6-Oxoverdazyl Radicals
  作者：Matthew Bancerz、Beom Youn、Matthew V. DaCosta、Michael K. Georges

  DOI：10.1021/jo300027b

  日期：2012.3.2

  A complementary approach to published synthetic methods for tetrazinanones, precursors to verdazyl radicals, is described herein. This approach uses carbohydrazide, a commercially available reagent, as a common starting material. Unlike previous methods described in the literature, this synthetic scheme does not rely on phosgene, phosgene substitutes, or the limited pool of commercially available monosubstituted

  本文描述了对四氮杂酮（Verdazyl自由基的前体）的公开合成方法的补充方法。该方法使用可商购的试剂碳酰肼作为常见的起始原料。与文献中描述的先前方法不同，该合成方案不依赖于光气，光气替代物或有限的市售单取代肼来执行。在verdazyl自由基的N-1和N-5位置上，可能会有各种各样的烷基取代方式，包括对称和不对称取代的产物。碳酰肼与特定醛的初始缩合反应在最终的Verdazyl自由基产物中引入了所需的C-3取代基并保护了NH 2在随后的N-1和N-5烷基化反应过程中产生的基团。随后的甲醇分解和伴随的闭环反应得到四嗪酮。然后可以采用许多已知的氧化方法来形成最终的Verdazyl自由基产物。
• Synthesis of Novel Triazoles, Tetrazine, Thiadiazoles and Their Biological Activities
  作者：Mohammed Al-Omair、Abdelwahed Sayed、Magdy Youssef

  DOI：10.3390/molecules20022591

  日期：——

  An expedient synthesis of novel triazoles, tetrazine and thiadiazoles, using conveniently accessible and commercially available starting materials has been achieved. The synthesized compounds were characterized by spectroscopic and elemental analyses, and screened for their antibacterial activities against four different strains, namely E. coli, P. aeruginosa, S. aureus and B. megaterium. In particular, the compounds 5, 24 and 26h exhibited excellent antibacterial activities compared to the reference antibiotic. To get further insight about their behavior, these compounds were tested for their antioxidant activities via SOD-like activity, DPPH free radical scavenging activity, ABST and NO, which showed promising results. Furthermore, these compounds effectively promoted the cleavage of genomic DNA as well, in the absence of any external additives.

  利用方便易得的市售起始材料，实现了新型三唑、四氮杂嗪和噻二唑的快速合成。通过光谱和元素分析对合成的化合物进行了表征，并筛选了它们对四种不同菌株（即大肠杆菌、铜绿假单胞菌、金黄色葡萄球菌和巨大芽孢杆菌）的抗菌活性。与参考抗生素相比，化合物 5、24 和 26h 尤其表现出卓越的抗菌活性。为了进一步了解这些化合物的行为，研究人员通过 SOD 样活性、DPPH 自由基清除活性、ABST 和 NO 测试了它们的抗氧化活性。此外，在没有任何外部添加剂的情况下，这些化合物还能有效促进基因组 DNA 的裂解。
• Unusual product from the acid-catalyzed one-pot, multicomponent reaction of thiocarbohydrazide, aldehydes, and phenacyl bromides
  作者：Mohanad Shkoor、Ayahtallah Al-Abade、Ibtesam Aleteiwib、Mahmoud Al-Talib、Hasan Tashtoush

  DOI：10.1080/00397911.2017.1332225

  日期：2017.8.18

  five-membered thiazole ring bonded to two hydrazone motifs is described. The acid-catalyzed reaction of one equivalent of thiocarbohydrazide, two equivalents of aromatic aldehydes, and one equivalent of phenacyl bromides afforded the five-membered thiazole ring. The reactions proceed with novel chemoselectivity. Similar reported protocols have always afforded 1,3,4-thiadiazines. GRAPHICAL ABSTRACT

  摘要描述了一种用于合成与两个腙基序结合的新型五元噻唑环的一锅三组分方案。一当量的硫代碳酰肼、两当量的芳香醛和一当量的苯甲酰溴在酸催化下反应得到五元噻唑环。反应以新的化学选择性进行。类似的报道协议一直提供 1,3,4-噻二嗪。图形概要
• Novel Synthesis of Oxothiazolidine Derivatives
  作者：Alaa A. Hassan、Yusria R. Ibrahim、Essmat M. El-Sheref、Alan B. Brown

  DOI：10.1002/jhet.935

  日期：2012.9

  (Z)‐Methyl 2‐[3‐(arylideneamino)‐2‐(arylidenehydrazono)‐4‐oxothiazolidin‐5‐ylidene]acetate prepared during the reaction between thiocarbonohydrazides and dimethyl acetylene dicarboxylate. Rational for there conversations involving the nucleophilic addition on C/C triple bond of dimethyl acetylenedicarboxylate are presented.

  （Z）-2-硫代碳酰肼与二甲基乙炔二甲酯反应时制得的2- [3-（3-亚芳基氨基）-2-（芳基亚氮杂基）-4-氧噻唑啉--5-亚苄基]乙酸酯。提出了有关乙炔二羧酸二甲酯的C / C三键亲核加成的讨论的合理性。