2-噻吩羧酸,2-[[(苯基甲基)氨基]硫代甲基]酰肼 | 139614-66-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 2-噻吩羧酸,2-[[(苯基甲基)氨基]硫代甲基]酰肼
• 英文名称: N-benzyl-2-(thiophene-2-carbonyl)hydrazine-1-carbothioamide
• 英文别名: N-benzyl-2-(thien-2-ylcarbonyl)hydrazinecarbothioamide；4-Benzyl-1-(thiophene-2-carbonyl)thiosemicarbazide；1-benzyl-3-(thiophene-2-carbonylamino)thiourea
• CAS: 139614-66-7
• 化学式: C₁₃H₁₃N₃OS₂
• mdl: MFCD04243678
• 分子量: 291.398
• InChiKey: KTDDISKKWZFBAD-UHFFFAOYSA-N

物化性质

• 密度：
  1.330±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-噻吩羧酸,2-[[(苯基甲基)氨基]硫代甲基]酰肼 在 吡啶 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以82%的产率得到N-benzyl-(5-thiophen-2-yl-[1,3,4]oxadiazol-2-yl)-amine
  参考文献：
  名称：

  Superior Reactivity of Thiosemicarbazides in the Synthesis of 2-Amino-1,3,4-oxadiazoles

  摘要：

  A facile and general protocol for the preparation of 2-amino-1,3,4- oxadiazoles is reported. This method relies on a tosyl chloride/pyridine-mediated cyclization of a thiosemicarbazide, which is readily prepared by acylation of a given hydrazide with the appropriate isothiocyanate. Cyclization of the thiosemicarbazide consistently outperforms the analogous semicarbazide cyclization under these conditions, for 18 distinct examples. Utilizing this protocol, we have prepared 5-alkyl- and 5-aryl-2-amino-1,3,4-oxadiazoles in 78-99% yield.

  DOI：

  10.1021/jo0618730
• 作为产物：
  描述：

  2-噻吩甲酰肼 、 异硫氰酸苯甲酯 在 盐酸 作用下， 以 乙醇 为溶剂， 生成 2-噻吩羧酸,2-[[(苯基甲基)氨基]硫代甲基]酰肼
  参考文献：
  名称：

  1-[3-甲基-3-(2,4,6-三甲基苯基)环丁基]-2-{[4-(芳基/烷基)-5-(噻吩-2-基)的合成、表征和量子化学计算)-4H-1,2,4-三唑-3-基]硫烷基}乙酮衍生物

  摘要：

  摘要 1-[3-甲基-3-(2,4,6-三甲基苯基)环丁基]-2-{[4-苄基(4-甲基苯基)-5-(噻吩-2-基)-4 H -1,2 2-氯-1-[3-甲基-3-(2,4,6-三甲基苯基)环丁基]乙酮与4-苄基-和4缩合合成了2-氯-1-[3-甲基-3-(2,4,6-三甲基苯基)环丁基]乙酮。 -(4-甲基苯基)-5-(噻吩-2-基)-4H - 1,2,4-三唑-3-硫醇。新化合物通过 FT-IR 以及1 H 和13 C NMR 谱进行了表征。使用密度泛函方法 (B3LYP )和6–311G ( d , p ) 基组。计算结果表明，优化后的几何结构很好地再现了理论振动频率，计算的化学位移与实验值吻合良好。

  DOI：

  10.1134/s1070428024010135

文献信息

• Triazole derivatives and method of using the same to treat HIV infections
  申请人：Olson Matthew

  公开号：US20050209287A1

  公开（公告）日：2005-09-22

  The present invention is directed to compounds of formula (I): wherein R 1 , R 2 and R 3 are independently selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, aryl and heteroaryl and X 1 and X 2 are independently a bond or an linker group of 1 to 6 atoms and may be optional substituted or oxidized, or a prodrug, a pharmaceutically acceptable salt or a pharmaceutically active metabolite thereof. The invention is also directed to methods of using the same for treating HIV infections, or AIDs or preventing viral replication.

  本发明涉及以下式(I)的化合物：其中R1、R2和R3分别独立地选择自烷基、烯基、炔基、环烷基、芳基和杂芳基的群组，X1和X2独立地为1至6个原子的键或连接基，并且可以是可选择取代或氧化的，或者是一个前药、药学上可接受的盐或其药理活性代谢物。该发明还涉及使用相同的方法来治疗HIV感染，或艾滋病，或预防病毒复制。
• Facile Synthesis of Naphtho[2,3-<i>d</i>]thiazoles, Naphtho[2,3-<i>e</i>][1,3,4]thiadiazines and Bis(naphtho[2,3-<i>d</i>]thiazolyl)copper(II) Derivatives from Heteroylthiosemicarbazides
  作者：Alaa A. Hassan、Nasr K. Mohamed、Lamiaa E. Abd El-Haleem、Stefan Bräse、Martin Nieger

  DOI：10.1002/cjoc.201600195

  日期：2016.8

  A one step synthesis protocol for the conversion of heteroylthiosemicarbazides and 2,3‐dichloro‐1,4‐naphthoquinone to naphtho[2,3‐d]thiazoles, naphtho[2,3‐e][1,3,4]thiadiazines as well as bis(naphtho[2,3‐d]thiazolyl)copper(II) derivatives is described. The products were conclusively confirmed by single crystal X‐ray analyses. A mechanism for the formation of the products is presented.

  一步合成方案，用于将杂芳基硫代氨基脲和2,3-二氯-1,4-萘醌转化为萘并[2,3- d ]噻唑，萘并[2,3- e ] [1,3,4]噻二嗪以及双（萘[2,3- d ]噻唑基）铜（II）衍生物的描述。产品通过单晶X射线分析最终确认。提出了形成产物的机制。
• Searching for novel scaffold of triazole non-nucleoside inhibitors of HIV-1 reverse transcriptase
  作者：Tomasz Frączek、Agata Paneth、Rafał Kamiński、Agnieszka Krakowiak、Piotr Paneth

  DOI：10.3109/14756366.2015.1039531

  日期：——

  Azoles are a promising class of the new generation of HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs). From thousands of reported compounds, many possess the same basic structure of an aryl substituted azole ring linked by a thioglycolamide chain with another aromatic ring. In order to find novel extensions for this basic scaffold, we explored the 5-position substitution pattern of triazole NNRTIs using molecular docking followed by the synthesis of selected compounds. We found that heterocyclic substituents in the 5-position of the triazole ring are detrimental to the inhibitory activity of compounds with four-membered thioglycolamide linker and this substitution seems to be viable only for compounds with shorter two-membered linker. Promising compound, N-(4-carboxy-2-chlorophenyl)-2-((4-benzyl-5-methyl-4H-1,2,4-triazol-3-yl)sulfanyl)acetamide, with potent inhibitory activity and acceptable aqueous solubility has been identified in this study that could serve as lead scaffold for the development of novel water-soluble salts of triazole NNRTIs.
• Triazole derivatives as non-nucleoside inhibitors of HIV-1 reverse transcriptase—Structure–activity relationships and crystallographic analysis
  作者：Thorsten A. Kirschberg、Mini Balakrishnan、Wei Huang、Rebecca Hluhanich、Nilima Kutty、Albert C. Liclican、Damian J. McColl、Neil H. Squires、Eric B. Lansdon

  DOI：10.1016/j.bmcl.2007.11.127

  日期：2008.2

  A series of 3,4,5-trisubstituted 1,2,4-4H triazole derivatives was synthesized and investigated for HIV-1 reverse transcriptase inhibition. An X-ray structure with HIV-1 RT secured the binding mode and allowed the key interactions with the enzyme to be identified.
• Small molecule inhibitors of HIV RT Ribonuclease H
  作者：Martin Di Grandi、Matthew Olson、Amar S. Prashad、Geraldine Bebernitz、Amara Luckay、Stanley Mullen、Yongbo Hu、Girija Krishnamurthy、Keith Pitts、John O’Connell

  DOI：10.1016/j.bmcl.2009.10.043

  日期：2010.1

  Two classes of compounds, thiocarbamates 1 and triazoles 2, have been identified as HIV RT RNase H inhibitors using a novel FRET-based HTS assay. The potent analogs in each series exhibited selectivity and were active in cell-based assays. In addition, saturable, 1: 1 stoichiometric binding to target was established and time of addition studies were consistent with inhibition of RT-mediated HIV replication. (C) 2009 Elsevier Ltd. All rights reserved.