2-chloro-5-(5-formylfuran-2-yl)nicotinic acid | 1190223-48-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-chloro-5-(5-formylfuran-2-yl)nicotinic acid
• 英文别名: 2-Chloro-5-(5-formylfuran-2-yl)pyridine-3-carboxylic acid
• CAS: 1190223-48-3
• 化学式: C₁₁H₆ClNO₄
• 分子量: 251.626
• InChiKey: SVSWKHMOBAURCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(2-苯乙基)-2-硫代-1,3-噻唑烷-4- 、 2-chloro-5-(5-formylfuran-2-yl)nicotinic acid 在 2,2,6,6-四甲基哌啶 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以49%的产率得到2-chloro-5-{5-[4-oxo-3-phenethyl-2-thioxothiazolidin-5-ylidenemethyl]furan-2-yl}nicotinic acid
  参考文献：
  名称：

  Design, Synthesis, and Structure−Activity Relationship of a Novel Series of 2-Aryl 5-(4-Oxo-3-phenethyl-2-thioxothiazolidinylidenemethyl)furans as HIV-1 Entry Inhibitors

  摘要：

  We previously identified two small molecules targeting the HIV-1 gp41, N-(4-carboxy-3-hydroxy)phenyl-2,5-dimethylpyrrole 12 (NB-2) and N-(3-carboxy-4-chloro)phenylpyrrole 13 (NB-64), that inhibit HIV-1 infection at low micromolar levels. Oil the basis of molecular docking analysis, we designed a series of 2-aryl 5-(4-oxo-3-phenethyl-2-thioxothiazolidinylidenemethyl)furans. Compared with 12 and 13, these compounds have bigger molecular size (437-515 Da) and could occupy more space in the deep hydrophobic pocket oil the gp41 NHR trimer. Fifteen 2-aryl 5-(4-oxo-3-phenethyl-2-thioxothiazolidinylidenemethyl)furans (11a-o) were synthesized by Suzuki-Miyaura cross-coupling followed by a Knoevenagel condensation and tested for their anti-HIV-1 activity and cytotoxicity on MT-2 cells. We found that all 15 compounds had improved anti-HIV-1 activity and 3 of them (11a, 11b, and 11d) exhibited inhibitory activity against replication of HIB-1(IIIB) and 94UG103 at < 100 nM range, more than 20-fold more potent than 12 and 13, suggesting that these Compounds can serve as leads for development of novel small molecule HIV fusion inhibitors.

  DOI：

  10.1021/jm900450n
• 作为产物：
  描述：

  5-甲醛基呋喃-2-硼酸 、 5-溴-2-氯烟酸 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 反应 28.0h， 以28%的产率得到2-chloro-5-(5-formylfuran-2-yl)nicotinic acid
  参考文献：
  名称：

  Design, Synthesis, and Structure−Activity Relationship of a Novel Series of 2-Aryl 5-(4-Oxo-3-phenethyl-2-thioxothiazolidinylidenemethyl)furans as HIV-1 Entry Inhibitors

  摘要：

  We previously identified two small molecules targeting the HIV-1 gp41, N-(4-carboxy-3-hydroxy)phenyl-2,5-dimethylpyrrole 12 (NB-2) and N-(3-carboxy-4-chloro)phenylpyrrole 13 (NB-64), that inhibit HIV-1 infection at low micromolar levels. Oil the basis of molecular docking analysis, we designed a series of 2-aryl 5-(4-oxo-3-phenethyl-2-thioxothiazolidinylidenemethyl)furans. Compared with 12 and 13, these compounds have bigger molecular size (437-515 Da) and could occupy more space in the deep hydrophobic pocket oil the gp41 NHR trimer. Fifteen 2-aryl 5-(4-oxo-3-phenethyl-2-thioxothiazolidinylidenemethyl)furans (11a-o) were synthesized by Suzuki-Miyaura cross-coupling followed by a Knoevenagel condensation and tested for their anti-HIV-1 activity and cytotoxicity on MT-2 cells. We found that all 15 compounds had improved anti-HIV-1 activity and 3 of them (11a, 11b, and 11d) exhibited inhibitory activity against replication of HIB-1(IIIB) and 94UG103 at < 100 nM range, more than 20-fold more potent than 12 and 13, suggesting that these Compounds can serve as leads for development of novel small molecule HIV fusion inhibitors.

  DOI：

  10.1021/jm900450n

文献信息

• Design, Synthesis, and Structure−Activity Relationship of a Novel Series of 2-Aryl 5-(4-Oxo-3-phenethyl-2-thioxothiazolidinylidenemethyl)furans as HIV-1 Entry Inhibitors
  作者：Alan R. Katritzky、Srinivasa R. Tala、Hong Lu、Anatoliy V. Vakulenko、Qi-Yin Chen、Jothilingam Sivapackiam、Keyur Pandya、Shibo Jiang、Asim K. Debnath

  DOI：10.1021/jm900450n

  日期：2009.12.10

  We previously identified two small molecules targeting the HIV-1 gp41, N-(4-carboxy-3-hydroxy)phenyl-2,5-dimethylpyrrole 12 (NB-2) and N-(3-carboxy-4-chloro)phenylpyrrole 13 (NB-64), that inhibit HIV-1 infection at low micromolar levels. Oil the basis of molecular docking analysis, we designed a series of 2-aryl 5-(4-oxo-3-phenethyl-2-thioxothiazolidinylidenemethyl)furans. Compared with 12 and 13, these compounds have bigger molecular size (437-515 Da) and could occupy more space in the deep hydrophobic pocket oil the gp41 NHR trimer. Fifteen 2-aryl 5-(4-oxo-3-phenethyl-2-thioxothiazolidinylidenemethyl)furans (11a-o) were synthesized by Suzuki-Miyaura cross-coupling followed by a Knoevenagel condensation and tested for their anti-HIV-1 activity and cytotoxicity on MT-2 cells. We found that all 15 compounds had improved anti-HIV-1 activity and 3 of them (11a, 11b, and 11d) exhibited inhibitory activity against replication of HIB-1(IIIB) and 94UG103 at < 100 nM range, more than 20-fold more potent than 12 and 13, suggesting that these Compounds can serve as leads for development of novel small molecule HIV fusion inhibitors.