1-phenyl-5-(prop-2-yn-1-ylthio)-1H-tetrazole | 53918-41-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-phenyl-5-(prop-2-yn-1-ylthio)-1H-tetrazole
• 英文别名: 1-Phenyl-1H-tetraazol-5-yl 2-propynyl sulfide；1-phenyl-5-prop-2-ynylsulfanyltetrazole
• CAS: 53918-41-5
• 化学式: C₁₀H₈N₄S
• mdl: MFCD02989493
• 分子量: 216.266
• InChiKey: IQGCLAHBIJSVEY-UHFFFAOYSA-N

物化性质

• 沸点：
  378.7±44.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  68.9
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-phenyl-5-(prop-2-yn-1-ylthio)-1H-tetrazole 、 p-叠氮甲苯 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到5-({[1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl]methyl}sulfanyl)-1-phenyl-1H-tetrazole
  参考文献：
  名称：

  Synthesis of 5-{[(1-Aryl-1H-1,2,3-triazol-4-yl)methyl]sulfanyl}-1-phenyl-1H-tetrazoles

  摘要：

  A series of novel 5-(1,2,3-triazolylmethylsulfanyl)tetrazole derivatives were synthesized by the click reaction from 1-phenyl-5-(prop-2-yn-1-ylsulfanyl)-1H-tetrazole and the corresponding azide. The reaction optimization results showed that higher yields are obtained using CuSO(4)and sodium ascorbate in DMF-water (2:1). The product structures were established on the basis of various spectral data, and their evaluation for antimicrobial activity showed moderate to good results compared to standard drugs.

  DOI：

  10.1134/s1070428020060172
• 作为产物：
  描述：

  硫代异氰酸苯酯 在 sodium azide 、 四丁基溴化铵 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 1-phenyl-5-(prop-2-yn-1-ylthio)-1H-tetrazole
  参考文献：
  名称：

  Synthesis of 5-{[(1-Aryl-1H-1,2,3-triazol-4-yl)methyl]sulfanyl}-1-phenyl-1H-tetrazoles

  摘要：

  A series of novel 5-(1,2,3-triazolylmethylsulfanyl)tetrazole derivatives were synthesized by the click reaction from 1-phenyl-5-(prop-2-yn-1-ylsulfanyl)-1H-tetrazole and the corresponding azide. The reaction optimization results showed that higher yields are obtained using CuSO(4)and sodium ascorbate in DMF-water (2:1). The product structures were established on the basis of various spectral data, and their evaluation for antimicrobial activity showed moderate to good results compared to standard drugs.

  DOI：

  10.1134/s1070428020060172

文献信息

• [EN] EXPANDED THERAPEUTIC POTENTIAL IN NITROHETEROARYL ANTIMICROBIALS<br/>[FR] POTENTIEL THÉRAPEUTIQUE ÉTENDU DANS DES ANTIMICROBIENS À NITROHÉTÉROARYLE
  申请人：UNIV CALIFORNIA

  公开号：WO2014205414A1

  公开（公告）日：2014-12-24

  Disclosed herein are antimicrobial compounds compositions, pharmaceutical compositions, the use and preparation thereof. Some embodiments relate to imidazole, thiazole, and furan derivatives and their use as therapeutic agents.

  本文披露了抗微生物化合物组合物、药物组合物及其使用和制备。一些实施例涉及咪唑、噻唑和呋喃衍生物及其作为治疗剂的用途。
• Convenient synthesis of allylic sulfides and application to allylic carbon-carbon bond formation.
  作者：Kanoko TSUBOYAMA、Kazuyoshi TAKEDA、Katsumi TORII、Haruo OGURA

  DOI：10.1248/cpb.38.2357

  日期：——

  Allylic sulfides were synthesized from allylic alcohols 1 using S, S'-bis(1-phenyl-1H-tetrazol-5-yl) dithiocarbonate (2) by means of a single-step reaction. The allylic sulfides were coupled with a Grignard reagent or carbanion in the presence of a catalytic amount of copper(I) bromide or palladium(0).

  阿利基硫化物通过一步反应，由阿利基醇1与S,S'-双(1-苯基-1H-四唑-5-基)二硫代碳酸酯2合成。这些阿利基硫化物在催化量的铜(I)溴化物或钯(0)存在下，与格氏试剂或碳负离子进行偶联反应。
• Single-step preparation of allylic sulfides having 1-phenyltetrazole-5-thio group from allylic alcohols using ,′-BIS(1-phenyl-1-tetrazol-5-YL) dithiocarbonate and reactions involving the allylic sulfides
  作者：Kazuyoshi Takeda、Kanoko Tsuboyama、Katsumi Torii、Maki Murata、Haruo Ogura

  DOI：10.1016/s0040-4039(00)80428-1

  日期：1988.1

  The reaction of allylic alcohols and ,′-bis(1-phenyl-1-tetrazol-5-yl) dithiocarbonate () gave allylic sulfides having 1-phenyltetrazole-5-thio group in a single step. Furthermore, these allylic sulfides could be applied to carbon-carbon bond and carbon-sulfur bond formations by using Grignard reagents or carbanions in the presence of a catalytic amount of copper(I)bromide or palladium (0), respectively

  烯丙醇和的反应，双（1-苯基-1-四唑-5-基）二硫代碳酸酯（），得到具有在一个单一的步骤1苯基四唑基-5-硫代基烯丙基硫化物。此外，在催化量的溴化铜（I）或钯（0）的存在下，分别使用格氏试剂或碳负离子，可以将这些烯丙基硫化物应用于碳-碳键和碳-硫键的形成。
• Sweet Drugs for Bad Bugs: A Glycomimetic Strategy against the DC-SIGN-Mediated Dissemination of SARS-CoV-2
  作者：Jonathan Cramer、Adem Lakkaichi、Butrint Aliu、Roman P. Jakob、Sebastian Klein、Ivan Cattaneo、Xiaohua Jiang、Said Rabbani、Oliver Schwardt、Gert Zimmer、Matias Ciancaglini、Tiago Abreu Mota、Timm Maier、Beat Ernst

  DOI：10.1021/jacs.1c06778

  日期：2021.10.27

  screening hit yielded a glycomimetic ligand with a more than 100-fold improved binding affinity compared to methyl α-d-mannopyranoside. Analysis of binding thermodynamics revealed an enthalpy-driven improvement of binding affinity that was enabled by hydrophobic interactions with a loop region adjacent to the binding site and displacement of a conserved water molecule. The identified ligand was employed

  C 型凝集素受体 DC-SIGN 是一种在巨噬细胞和树突细胞上表达的模式识别受体。它已被确定为许多病原体的混杂进入受体，包括流行病和大流行病毒，如 SARS-CoV-2、埃博拉病毒和 HIV-1。在最近的 SARS-CoV-2 大流行的背景下，DC-SIGN 介导的病毒传播和先天免疫反应的刺激被认为是严重 COVID-19 发展的潜在因素。因此，抑制病毒与 DC-SIGN 的结合代表了一种有吸引力的宿主导向策略，以减弱先天免疫反应的过度反应并防止疾病的进展。在这项研究中，我们报告了从基于三唑的甘露糖类似物的重点库中发现的一类新的强效糖模拟物 DC-SIGN 拮抗剂。d-吡喃甘露糖苷。结合热力学分析揭示了焓驱动的结合亲和力的提高，这是通过与结合位点相邻的环区域的疏水相互作用和保守水分子的置换来实现的。所标识的配位体用于该能够抑制SARS-CoV的-2刺突糖蛋白结合DC-SIGN表达细胞的多价
• <i>Retracted:</i> Synthesis, Molecular Properties, and Biological Evaluation of Hybrid 1,2,3‐Triazolylpolyaza Heterocyclic Compounds
  作者：Srinivasa Rao Dasari、Subbaiah Tondepu、Lakshmana Rao Vadali、Mutyala Naidu Ganivada、Nareshvarma Seelam

  DOI：10.1002/jhet.3395

  日期：2019.1

  this research article, a highly efficient, cost‐effective synthesis of various hybrid molecules possessing 1,2,3‐triazolyltetrazoles and evaluation of their biological activity have been addressed. The structure elucidation of these new library hybrid molecules has been carried out by IR, 1H NMR, 13C NMR, and mass spectral analysis. The compounds have been screened for their anticancer activity against

  在这篇研究文章中，已经解决了具有1,2,3-三唑基四唑的各种杂合分子的高效，经济高效的合成及其生物活性的评价。这些新文库杂合分子的结构阐明已通过IR，1 H NMR，13 C NMR和质谱分析进行。筛选了这些化合物对人结肠癌细胞系Colo-205和人肺癌细胞HOP-205的抗癌活性，结果证明大多数化合物显示出非常好的治疗性质。特别是化合物3d，3j，6a和6e与阿霉素相比，它们对所有测试的人类癌细胞系的细胞毒性更高，分别增长68％，101.8％，94％和104.5％。在本研究中，对3a – j和6a – h系列进行了分子特性预测，Molinspiration进行了药物相似性评估以及Molsoft软件程序进行了毒性风险分析。所有18种类似物均基于Lipinski的“ 5条规则”进行合成，筛选其抗菌和抗癌药物为口服生物可利用药物/铅。