(quinazolin-4-ylthio)acetic acid | 63586-46-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (quinazolin-4-ylthio)acetic acid
• 英文别名: (4-quinazolinylthio)acetic acid；quinazolin-4-ylsulfanyl-acetic acid；CB-21；(Quinazolin-4-ylsulfanyl)-acetic acid；2-quinazolin-4-ylsulfanylacetic acid
• CAS: 63586-46-9
• 化学式: C₁₀H₈N₂O₂S
• mdl: MFCD00723190
• 分子量: 220.252
• InChiKey: UZMKTFWOCNJXGI-UHFFFAOYSA-N

物化性质

• 熔点：
  205-206 °C(Solv: acetone (67-64-1))
• 沸点：
  446.1±25.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 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：
  88.4
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  (quinazolin-4-ylthio)acetic acid 在 乙酸酐 、 三乙胺 作用下， 以 吡啶 、 乙腈 为溶剂， 反应 0.5h， 生成 2-(4-nitrophenylaza)thiazolo<3,2-c>quinazolinium 3-oxide
  参考文献：
  名称：

  Mesoionic compounds with a bridged nitrogen atom.

  摘要：

  DOI：

  10.1007/bf00472399
• 作为产物：
  描述：

  4-羟基喹唑啉 在 劳森试剂 、 甲醇 、 氢化钾 作用下， 以 1,4-二氧六环 为溶剂， 生成 (quinazolin-4-ylthio)acetic acid
  参考文献：
  名称：

  2-Alkyl(aryl)-quinazolin-4(3H)-thiones, 2-R-(quinazolin-4(3H)-ylthio)carboxylic acids and amides: synthesis, molecular docking, antimicrobial and anticancer properties

  摘要：

  In this study, a series of novel 2-alkyl(aryl)-quinazolin-4(3H)-thiones, 2-R-(quinazolin-4(3H)-ylthio)carboxylic acids and amides were synthesized and evaluated for antimicrobial and anticancer activities. Their structure was confirmed by elemental analysis and spectral data (FT-IR, LC-MS, H-1-NMR). Antimicrobial activity was tested in vitro against Staphylococcus aureus, Enterococcus faecalis, Enterobacter aerogenes, Pseudomonas aeruginosa, Escherichia coli, Klebsiella pneumonia, Candida albicans and NCI in vitro preliminary anticancer activity against nine different cancer types. The most active antibacterial and antifungal compounds were: 2.1, 2.2 and 2.4. The introduction of the carboxylic acid or amide residue into the fourth position of quinazolin-4(3H)-thione resulted in the absence of antimicrobial activity. Substance 3.8 inhibited renal cancer UO-31 line and 2.18 - leukemia CCRF-CEM. The results of in silico molecular docking for DHFR and CK2 kinase had no correlation with in vitro properties, proposing the presence of other biological activity pathways.

  DOI：

  10.3109/14756366.2015.1018243

文献信息

• Identification of non-peptidic cysteine reactive fragments as inhibitors of cysteine protease rhodesain
  作者：Danielle McShan、Stefan Kathman、Brittiney Lowe、Ziyang Xu、Jennifer Zhan、Alexander Statsyuk、Ifedayo Victor Ogungbe

  DOI：10.1016/j.bmcl.2015.08.074

  日期：2015.10

  Rhodesain, the major cathepsin L-like cysteine protease in the protozoan Trypanosoma brucei rhodesiense, the causative agent of African sleeping sickness, is a well-validated drug target. In this work, we used a fragment-based approach to identify inhibitors of this cysteine protease, and identified inhibitors of T. brucei. To discover inhibitors active against rhodesain and T. brucei, we screened a library of covalent fragments against rhodesain and conducted preliminary SAR studies. We envision that in vitro enzymatic assays will further expand the use of the covalent tethering method, a simple fragment-based drug discovery technique to discover covalent drug leads. (C) 2015 Elsevier Ltd. All rights reserved.
• Talukdar,P.B. et al., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1977, vol. 15B, p. 41 - 45
  作者：Talukdar,P.B. et al.

  DOI：——

  日期：——
• Mesoionic compounds with a bridging nitrogen atom
  作者：K. V. Fedotov、A. D. Kachkovskii、N. N. Romanov、A. I. Tolmachev

  DOI：10.1007/bf00472630

  日期：1989.1
• FEDOTOV, K. V.;ROMANOV, N. N., XIMIYA GETEROTSIKL. SOED.,(1989) N, S. 408-412
  作者：FEDOTOV, K. V.、ROMANOV, N. N.

  DOI：——

  日期：——
• TALUKDAR P. B.; SENGUPTA S. K.; DATTA A. K.; ROY T. K., INDIAN J. CHEM. <IJOC-AP>, 1977, B 15, NO 1, 41-45
  作者：TALUKDAR P. B.、 SENGUPTA S. K.、 DATTA A. K.、 ROY T. K.

  DOI：——

  日期：——