3-cyclohexyl-1H-1,2,4-triazole-5(4H)-thione | 27429-85-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-cyclohexyl-1H-1,2,4-triazole-5(4H)-thione
• 英文别名: 5-cyclohexyl-2,4-dihydro-[1,2,4]triazole-3-thione；3-Cyclohexyl-1,2,4-triazolin-5-thion；5-Cyclohexyl-1,2-dihydro-1,2,4-triazole-3-thione
• CAS: 27429-85-2
• 化学式: C₈H₁₃N₃S
• mdl: MFCD11108434
• 分子量: 183.277
• InChiKey: WVVOQISRKUBCIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  68.5
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-溴-1-(2,3-二氢-1,4-苯并二氧)乙酮 、 3-cyclohexyl-1H-1,2,4-triazole-5(4H)-thione 以 乙醇 为溶剂， 以26%的产率得到2-((3-cyclohexyl-1H-1,2,4-triazol-5-yl)thio)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)ethan-1-one
  参考文献：
  名称：

  Structure-activity relationships of triazole-benzodioxine inhibitors of cathepsin X

  摘要：

  Cathepsin X is a cysteine carboxypeptidase that is involved in various physiological and pathological processes. In particular, highly elevated expression and activity of cathepsin X has been observed in cancers and neurodegenerative diseases. Previously, we identified compound Z9 (1-(2,3-dihydrobenzo [b][1,4]dioxin-6-yl)-2-((4-isopropyl-4H-1,2,4-triazol-3-yl)thio)ethan-1-one) as a potent and specific reversible cathepsin X inhibitor. Here, we have explored the effects of chemical variations to Z9 of either benzodioxine or triazol moieties, and the importance of the central ketomethylenethio linker. The ketomethylenethio linker was crucial for cathepsin X inhibition, whereas changes of the triazole heterocycle did not alter the inhibitory potencies to a greater extent. Replacement of benzodioxine moiety with substituted benzenes reduced cathepsin X inhibition. Overall, several synthesized compounds showed similar or improved inhibitory potencies against cathepsin X compared to Z9, with IC50 values of 7.1 mu M-13.6 mu M. Additionally, 25 inhibited prostate cancer cell migration by 21%, which is under the control of cathepsin X. (c) 2020 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2020.112218
• 作为产物：
  描述：

  2-(cyclohexanecarbonyl)hydrazine-1-carbothioamide 在 sodium hydroxide 作用下， 反应 0.05h， 以83%的产率得到3-cyclohexyl-1H-1,2,4-triazole-5(4H)-thione
  参考文献：
  名称：

  基于2- {6- [2- [5-（苯基] -4H- {1,2,4]三唑-3-基硫基]乙酰氨基]苯并噻唑-2-基硫基}的西尼罗河病毒蛋白酶抑制剂的合成和体外评估乙酰胺支架

  摘要：

  近年来，由西尼罗河病毒（WNV）感染引起的临床症状严重程度恶化，老年人神经侵袭性疾病的发生频率增加。由于目前尚无成功的抗WNV疗法用于人类，因此迫切需要为开发新的针对该病毒的化学疗法而不断努力。由于其在病毒复制中的重要性及其独特的底物偏爱性，病毒NS2B-NS3蛋白酶是有希望的病毒抑制靶标。在这项研究中，WNV NS2B-NS3蛋白酶抑制剂具有2- {6- [2-（5-苯基-4H]在筛选过程中发现了[[1,2,4]三唑-3-基硫烷基]乙酰氨基]苯并噻唑-2-基硫基}乙酰胺支架。通过合成和的筛选该初始命中的优化聚焦化合物库与此支架导致的新颖非竞争性抑制剂的鉴定（1 A24，IC 50 = 3.4±0.2μ中号的WNV的NS2B-NS3蛋白酶）。1 a24分子对接至WNV蛋白酶表明该化合物干扰NS2B辅因子与NS3蛋白酶的生产性相互作用，并且是WNV NS3蛋白酶的变构抑制剂。

  DOI：

  10.1002/cmdc.201300114

文献信息

• Simple Synthesis of Fused Thiazolo[4,5-b]pyridines through Successive SNAr Processes
  作者：Alexey M. Starosotnikov、Maxim A. Bastrakov、Vadim V. Kachala、Ivan V. Fedyanin、Tatyana A. Klimova、Victoria V. Ivanova、Igor L. Dalinger

  DOI：10.1055/s-0040-1705960

  日期：2021.2

  A convenient process is described for the synthesis of novel thiazolo[4,5-b]pyridines fused with triazole or pyrimidine rings. The base-promoted reactions of 2-chloro-3-nitropyridines with 1,3-(S,N)-binucleophiles (triazole-5-thiols, 4-oxopyrimidine-2-thiones) resulted in nucleophilic substitution of the chlorine atom and subsequent S–N-type Smiles rearrangement followed by nucleophilic substitution

  描述了一种方便的方法，用于合成与三唑或嘧啶环稠合的新型噻唑并[4,5- b ]吡啶。2-氯-3-硝基吡啶与1,3-（S，N）-双亲核试剂（三唑-5-硫醇，4-氧嘧啶-2-硫酮）的碱促进反应导致氯原子的亲核取代，随后S–N型Smiles重排，然后进行硝基的亲核取代。与嘧啶-2-硫酮的反应以一锅法进行，而在三唑-5-硫醇的情况下，发现分离中间取代产物是优选的。
• Novel compound, polymerizable composition, color filter and production method thereof, solid-state imaging device, and planographic printing plate precursor
  申请人：FUJIFILM Corporation

  公开号：EP2141206A1

  公开（公告）日：2010-01-06

  A photopolymerizable composition is obtained which has a high sensitivity to light sources having wavelengths of around 365 nm, excellent storage stability, and can form a cured film which can prevent deterioration in film properties thereof due to heat aging. The photopolymerizable composition includes (A) an oxime polymerization initiator which has, in ethyl acetate, a molar absorption coefficient of 20,000 or more at a λmax within the wavelength range of 300 nm or more and less than 400 nm and a molar absorption coefficient of 400 or less at (λmax + 20 nm) and (B) a polymerizable compound.

  我们获得了一种可光聚合组合物，该组合物对波长约为 365 纳米的光源具有高灵敏度，贮存稳定性极佳，并可形成固化薄膜，防止因热老化而导致薄膜性能下降。该光聚合组合物包括 (A) 肟聚合引发剂，该引发剂在乙酸乙酯中，λmax 在波长范围 300 nm 以上 400 nm 以下时的摩尔吸收系数为 20,000 或更高，(λmax + 20 nm) 时的摩尔吸收系数为 400 或更低，以及 (B) 可聚合化合物。