(E)-2-(cyclohexylmethylene)hydrazinecarbothioamide | 1334180-05-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E)-2-(cyclohexylmethylene)hydrazinecarbothioamide
• 英文别名: (E)-2-(cyclohexylmethylene)hydrazine-1-carbothioamide；(E)-cyclohexanecarbaldehyde thiosemicarbazone；2-(Cyclohexylmethylidene)hydrazine-1-carbothioamide；[(E)-cyclohexylmethylideneamino]thiourea
• CAS: 1334180-05-0
• 化学式: C₈H₁₅N₃S
• 分子量: 185.293
• InChiKey: BIABXHSWAUGGPM-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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-溴-4'-氰基苯乙酮 、 (E)-2-(cyclohexylmethylene)hydrazinecarbothioamide 以 乙醇 为溶剂， 反应 20.0h， 以94%的产率得到(E)-4-(2-(2-(cyclohexylmethylene)hydrazinyl)thiazol-4-yl)benzonitrile
  参考文献：
  名称：

  Synthesis, antimicrobial evaluation and theoretical prediction of NMR chemical shifts of thiazole and selenazole derivatives with high antifungal activity against Candida spp.

  摘要：

  Synthesis and investigation of antimicrobial activities of novel thiazoles and selenazoles is presented. Their structures were determined using NMR, FAB(+)-MS, HRMS and elemental analyses. To support the experiment, theoretical calculations of the H-1 NMR shifts were carried out for representative systems within the DFT B3LYP/6-311++G** approximation which additionally confirmed the structure of investigated compounds. Among the derivatives, compounds 4b, 4h, 4j and 4l had very strong activity against reference strains of Candida albicans ATCC and Candida parapsilosis ATCC 22019 with MIC = 0.49 -7.81 mu g/ml. In the case of compounds 4b, 4c, 4h - 4j and 4l, the activity was very strong against of Candida spp. isolated from clinical materials, i.e. C. albicans, Candida krusei, Candida inconspicua, Candida famata, Candida lusitaniae, Candida sake, C. parapsilosis and Candida dubliniensis with MIC = 0.24 -15.62 mu g/ml. The activity of several of these was similar to the activity of commonly used antifungal agent fluconazole. Additionally, compounds 4m - 4s were found to be active against Gram-positive bacteria, both pathogenic staphylococci Staphylococcus aureus ATCC with MIC = 31.25-125 mu g/ml and opportunistic bacteria, such as Staphylococcus epidermidis ATCC 12228 and Micrococcus luteus ATCC 10240 with MIC = 7.81-31.25 mu g/ml. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2015.12.033
• 作为产物：
  描述：

  氨基硫脲 、 环己烷基甲醛 在 四氢吡咯 作用下， 以 水 为溶剂， 反应 0.58h， 生成 (E)-2-(cyclohexylmethylene)hydrazinecarbothioamide
  参考文献：
  名称：

  在温和的有机催化反应条件下可持续合成肟，Hy和硫代氨基脲

  摘要：

  吡咯烷很有效地催化，大概是通过亚胺基活化，使用等摩尔量的试剂和绿色溶剂，形成了芳香族和脂肪族醛衍生的酰基肟，酰基hydr和硫代半氨基甲酮。该方法的主要优点是实验简单，过滤简单后的优异收率，是目前可用于那些特别是酰基衍生物的替代方法，这些方法在未催化条件下不起作用。通过醛和酰基羟胺之间的直接缩合将其用于合成酰基肟的应用是空前的。

  DOI：

  10.1021/acs.joc.6b01912

文献信息

• TIRE RUBBER COMPOSITION AND MANUFACTURING METHOD THEREFOR
  申请人：Bridgestone Corporation

  公开号：EP3006496A1

  公开（公告）日：2016-04-13

  The present invention provides a tire rubber composition prepared by mixing at least one rubber component selected from natural rubbers and synthetic diene rubbers (A), a filler including an inorganic filler (B), a silane coupling agent (C) and a thiosemicarbazone derivative (D), and provides a production method for a tire rubber composition, wherein the tire rubber composition is kneaded in plural stages, and in the first stage of kneading, the rubber component (A), all or part of the inorganic filler (B), all or part of the silane coupling agent (C), and the thiosemicarbazone derivative (D) are kneaded, therefore providing a tire rubber composition having improved reactivity between the coupling agent and the rubber component and excellent in low-heat-generation property and a production method for the composition.

  本发明提供了一种通过混合至少一种选自天然橡胶和合成二烯橡胶的橡胶组分（A）、包括无机填料（B）在内的填料、硅烷偶联剂（C）和硫代氨基脲衍生物（D）制备的轮胎橡胶组合物，并提供了一种轮胎橡胶组合物的生产方法，其中轮胎橡胶组合物经过多个阶段的捏合、在第一阶段捏合过程中，捏合橡胶成分（A）、全部或部分无机填料（B）、全部或部分硅烷偶联剂（C）和硫代氨基脲衍生物（D），从而提供一种轮胎橡胶组合物，该组合物具有更好的偶联剂与橡胶成分之间的反应性和优异的低发热性能，并提供一种该组合物的生产方法。
• Structural characteristics of thiosemicarbazones as inhibitors of melanogenesis
  作者：Ki-Cheul Lee、Pillaiyar Thanigaimalai、Vinay K. Sharma、Min-Seok Kim、Eunmiri Roh、Bang-Yeon Hwang、Youngsoo Kim、Sang-Hun Jung

  DOI：10.1016/j.bmcl.2010.08.114

  日期：2010.11

  A series of thiosemicarbazones 2(e-s) have been synthesized and studied their structure-activity relationship as melanogenesis inhibitor. Among them, (Z)-2-(naphthalen-1-ylmethylene) hydrazinecarbothioamide (2q, >100% inhibition at 10 mu M, IC50 = 1.1 mu M, C log P = 3.039) showed the strongest inhibitory activity. Regarding their structure-activity relationship, the hydrophobic substituents regardless the position on phenyl ring of benzaldehyde thiosemicarbazones enhance the inhibitory activity. Furthermore, the aromatic group of benzaldehydethiosemicarbazones can be replaced with sterically bulky cyclohexyl. Thus, hydrophobicity of the aryl or alkyl group on hydrazine of thiosemicarbazones is determinant factor for their inhibitory activity in melanogenesis rather than planarity. (C) 2010 Elsevier Ltd. All rights reserved.
• Thiazole compounds with activity against Cryptococcus gattii and Cryptococcus neoformans in vitro
  作者：Nívea Pereira de Sá、Cleudiomar Inácio Lino、Nayara Cristina Fonseca、Beatriz Martins Borelli、Jonas Pereira Ramos、Elaine Maria Souza-Fagundes、Carlos Augusto Rosa、Daniel Assis Santos、Renata Barbosa de Oliveira、Susana Johann

  DOI：10.1016/j.ejmech.2015.07.032

  日期：2015.9

  Human cryptococcosis can occur as a primary or opportunistic infection and develop as an acute, subacute, or chronic, systemic infection involving different host organs. We evaluated the antifungal activity of thirteen compounds against Cryptococcus gattii and Cryptococcus neoformans in vitro, by assessing the toxicity of the compounds showing the greatest antifungal activity in VERO cells and murine macrophages. From these results, four compounds were considered promising for further studies because they displayed low cytotoxicity and significant antifungal activity. The heterocyclic compounds 1b, 1c, 1d, and 1m have antifungal activity levels between that of amphotericin B and fluconazole in vitro. The death curve of Cryptococcus spp. treated with these four compounds was similar to the curve obtained for amphotericin B, in that we observed a significant reduction in cell viability within the first 24 h of treatment. Additionally, we found that there was no effect when these compounds were combined with amphotericin and fluconazole, except for 1c, which antagonized the effect of amphotericin B against C. gattii, also reflected in the reduction of the post-antifungal effect (PAFE); however, this interaction did not alter the ergosterol content. The results shown in this paper reveal the discovery of novel thiazole compounds, which are easy to synthesize, and with potentially exhibit antifungal activity, and display low cytotoxicity in normal mammalian cells. These compounds can be used as prototypes for the design of new antifungal drugs against C gattii and C neoformans. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Synthesis, antimicrobial evaluation and theoretical prediction of NMR chemical shifts of thiazole and selenazole derivatives with high antifungal activity against Candida spp.
  作者：Krzysztof Z. Łączkowski、Katarzyna Motylewska、Angelika Baranowska-Łączkowska、Anna Biernasiuk、Konrad Misiura、Anna Malm、Berta Fernández

  DOI：10.1016/j.molstruc.2015.12.033

  日期：2016.3

  Synthesis and investigation of antimicrobial activities of novel thiazoles and selenazoles is presented. Their structures were determined using NMR, FAB(+)-MS, HRMS and elemental analyses. To support the experiment, theoretical calculations of the H-1 NMR shifts were carried out for representative systems within the DFT B3LYP/6-311++G** approximation which additionally confirmed the structure of investigated compounds. Among the derivatives, compounds 4b, 4h, 4j and 4l had very strong activity against reference strains of Candida albicans ATCC and Candida parapsilosis ATCC 22019 with MIC = 0.49 -7.81 mu g/ml. In the case of compounds 4b, 4c, 4h - 4j and 4l, the activity was very strong against of Candida spp. isolated from clinical materials, i.e. C. albicans, Candida krusei, Candida inconspicua, Candida famata, Candida lusitaniae, Candida sake, C. parapsilosis and Candida dubliniensis with MIC = 0.24 -15.62 mu g/ml. The activity of several of these was similar to the activity of commonly used antifungal agent fluconazole. Additionally, compounds 4m - 4s were found to be active against Gram-positive bacteria, both pathogenic staphylococci Staphylococcus aureus ATCC with MIC = 31.25-125 mu g/ml and opportunistic bacteria, such as Staphylococcus epidermidis ATCC 12228 and Micrococcus luteus ATCC 10240 with MIC = 7.81-31.25 mu g/ml. (C) 2015 Elsevier B.V. All rights reserved.
• Sustainable Synthesis of Oximes, Hydrazones, and Thiosemicarbazones under Mild Organocatalyzed Reaction Conditions
  作者：Sara Morales、José Luis Aceña、José Luis García Ruano、M. Belén Cid

  DOI：10.1021/acs.joc.6b01912

  日期：2016.10.21

  thiosemicarbazones derived from aromatic and aliphatic aldehydes using equimolar amounts of reagents and green solvents. Experimental simplicity and excellent yields after a simple filtration are the main advantages of the method, being an alternative to those currently available especially for the acyl derivatives, which do not work under uncatalyzed conditions. Its application to the synthesis of acyloximes by

  吡咯烷很有效地催化，大概是通过亚胺基活化，使用等摩尔量的试剂和绿色溶剂，形成了芳香族和脂肪族醛衍生的酰基肟，酰基hydr和硫代半氨基甲酮。该方法的主要优点是实验简单，过滤简单后的优异收率，是目前可用于那些特别是酰基衍生物的替代方法，这些方法在未催化条件下不起作用。通过醛和酰基羟胺之间的直接缩合将其用于合成酰基肟的应用是空前的。