3-chloro-N-(4-(4-chlorophenyl)thiazol-2-yl) propanamide | 99447-01-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-chloro-N-(4-(4-chlorophenyl)thiazol-2-yl) propanamide
• 英文别名: 3-chloro-N-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]propanamide
• CAS: 99447-01-5
• 化学式: C₁₂H₁₀Cl₂N₂OS
• mdl: MFCD01357408
• 分子量: 301.196
• InChiKey: HBHACEXGKVILBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-chloro-N-(4-(4-chlorophenyl)thiazol-2-yl) propanamide 在 四氯苯醌 、 三乙胺 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 乙醚 、 二氯甲烷 、 苯 为溶剂， 生成 N-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]-1H-pyrazole-5-carboxamide
  参考文献：
  名称：

  Padmavathi, Venkatapuram; Sreelatha, Tumma; Reddy, Putta Ramachandra, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 53B, # 10, p. 1295 - 1300

  摘要：

  DOI：
• 作为产物：
  描述：

  对氯苯乙酮 在 碘 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 3-chloro-N-(4-(4-chlorophenyl)thiazol-2-yl) propanamide
  参考文献：
  名称：

  Development of 2-amino-4-phenylthiazole analogues to disrupt myeloid differentiation factor 88 and prevent inflammatory responses in acute lung injury

  摘要：

  Myeloid differentiation primary response protein 88 (MyD88), an essential adapter protein used by toll like receptors (TLR), is a promising target molecule for the treatment of respiratory inflammatory diseases. Previous studies explored the activities of novel 2-amino-4-phenylthiazole analogue (6) in inflammation-induced cancer, and identified the analogue as an inhibitor of MyD88 toll/interleukin-1 receptor (TIR) homology domain dimerization. Here, we describe the synthesis of 47 new analogues by modifying different sites on this lead compound and assessed their anti-inflammatory activities in lipopolysaccharide-induced mouse primary peritoneal macrophages (MPMs). The most promising compound, 15d, was found to effectively interact with MyD88 protein and prevented formation of the MyD88 homodimeric complex. Furthermore, 15d showed in vivo anti-inflammatory activity in LPS-caused model of acute lung injury. This work provides new candidates as MyD88 inhibitors to combat inflammation diseases. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.09.068

文献信息

• Substituted thiazoles VII. Synthesis and antitumor activity of certain 2-(substituted amino)-4-phenyl-1,3-thiazole analogs
  作者：Ghada S. Hassan、Shahenda M. El-Messery、Fatmah A.M. Al-Omary、Hussein I. El-Subbagh

  DOI：10.1016/j.bmcl.2012.08.095

  日期：2012.10

  for their antitumor activity, at a single dose of 10 μM. Most of the investigated compounds exhibited broad-spectrum antitumor activity. Compounds 19 and 28 believed to be the most active members in this study, with MG-MID GI50, TGI, and LC50 values of 2.8, 11.4, 44.7; and 3.3, 13.1, 46.8, respectively. Compounds 19 and 28 proved to be nine and sevenfold more active than the standard antitumor drug 5-FU

  设计并合成了一系列新的2-乙酰氨基-或2-丙酰胺基-4-（4-取代的苯基）-1,3-噻唑（11 – 34）。化合物以10μM的单剂量接受美国国家癌症研究所（NCI）的体外抗肿瘤活性评估。大多数研究的化合物表现出广谱抗肿瘤活性。化合物19和28被认为是该研究中最活跃的成员，其MG-MID GI 50，TGI和LC 50值为2.8、11.4、44.7。和3.3、13.1、46.8。事实证明，化合物19和28的活性分别比标准抗肿瘤药物5-FU高9倍和7倍。
• Synthesis of Amido-linked Oxazolyl/Thiazolyl/Imidazolyl Pyrazoles and Isoxazoles
  作者：Padmavathi Venkatapuram、Sreelatha Tumma、Seenaiah Dandu、Premakumari Chokkappagari

  DOI：10.1002/jhet.2185

  日期：2015.5

  The amido‐linked oxazolyl/thiazolyl/imidazolyl pyrazoles and isoxazoles were prepared from the synthetic intermediates oxazolyl/thiazolyl/imidazolyl acrylamides adpoting1,3‐dipolar cycloaddition of nitrile imines and nitrile oxides.

  酰胺基连接的恶唑基/噻唑基/咪唑基吡唑和异恶唑是由合成中间体恶唑基/噻唑基/咪唑基丙烯酰胺与1,3-偶极环加成腈亚胺和氧化腈制备的。