5-(4-甲氧基苄基)-4-(4-甲氧基苯基)噻唑-2-胺 | 106511-67-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-(4-甲氧基苄基)-4-(4-甲氧基苯基)噻唑-2-胺
• 英文名称: 5-(4-methoxybenzyl)-4-(4-methoxyphenyl)thiazol-2-amine
• 英文别名: 4-(4-Methoxyphenyl)-5-[(4-methoxyphenyl)methyl]-1,3-thiazol-2-amine
• CAS: 106511-67-5
• 化学式: C₁₈H₁₈N₂O₂S
• 分子量: 326.419
• InChiKey: MCRIZDTWLBNYKA-UHFFFAOYSA-N

物化性质

• 熔点：
  174-176 °C
• 沸点：
  534.6±50.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  85.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(4-甲氧基苄基)-4-(4-甲氧基苯基)噻唑-2-胺 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 N,5-bis(4-methoxybenzyl)-4-(4-methoxyphenyl)thiazol-2-amine
  参考文献：
  名称：

  2,4,5-Trisubstituted thiazole derivatives: A novel and potent class of non-nucleoside inhibitors of wild type and mutant HIV-1 reverse transcriptase

  摘要：

  Novel 2,4,5-trisubstituted thiazole derivatives (TSTs) were designed and synthesized as HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs). Among the thirty-eight synthesized target compounds, thirty TSTs showed potent inhibition against HIV-1 replication in wild type HIV-1 at submicromolar concentrations (from 0.046 to 9.59 mu M). Compounds 21, 23 and 24 were also tested on seven NNRTI-resistant HIV-1 strains, and all exhibited inhibitory effects with fold changes in IC50 ranging from 2.6 to 111, which were better than those of nevirapine (15.6-fold-371-fold). Docking simulations of compound 24 revealed a reasonable mechanism for the binding mode, and three-dimensional quantitative structure activity relationship (3-DQSAR) studies on this novel series of TST further elucidated the structure-activity relationship (SAR). The results suggested the great potential of TSTs as a novel class of NNRTIs with antiviral efficacy and a good resistance profile. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.07.072
• 作为产物：
  描述：

  4'-甲氧基-3-(4-甲氧基苯基)苯丙酮 在 溴 作用下， 以 四氯化碳 、 乙醇 为溶剂， 生成 5-(4-甲氧基苄基)-4-(4-甲氧基苯基)噻唑-2-胺
  参考文献：
  名称：

  Ahluwalia, V. K.; Kaila, Neelu; Bala, Shashi, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 502 - 504

  摘要：

  DOI：

文献信息

• Ahluwalia, V. K.; Kaila, Neelu; Bala, Shashi, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 502 - 504
  作者：Ahluwalia, V. K.、Kaila, Neelu、Bala, Shashi

  DOI：——

  日期：——
• AHLUWALIA V. K.; KAILA NEELU; BALA SHASHI, INDIAN J. CHEM., 25,(1986) N 5, 502-504
  作者：AHLUWALIA V. K.、 KAILA NEELU、 BALA SHASHI

  DOI：——

  日期：——
• 2,4,5-Trisubstituted thiazole derivatives: A novel and potent class of non-nucleoside inhibitors of wild type and mutant HIV-1 reverse transcriptase
  作者：Zhongliang Xu、Mingyu Ba、Hua Zhou、Yingli Cao、Chaojun Tang、Ying Yang、Ricai He、Yu Liang、Xuemei Zhang、Zhenzhong Li、Lihong Zhu、Ying Guo、Changbin Guo

  DOI：10.1016/j.ejmech.2014.07.072

  日期：2014.10

  Novel 2,4,5-trisubstituted thiazole derivatives (TSTs) were designed and synthesized as HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs). Among the thirty-eight synthesized target compounds, thirty TSTs showed potent inhibition against HIV-1 replication in wild type HIV-1 at submicromolar concentrations (from 0.046 to 9.59 mu M). Compounds 21, 23 and 24 were also tested on seven NNRTI-resistant HIV-1 strains, and all exhibited inhibitory effects with fold changes in IC50 ranging from 2.6 to 111, which were better than those of nevirapine (15.6-fold-371-fold). Docking simulations of compound 24 revealed a reasonable mechanism for the binding mode, and three-dimensional quantitative structure activity relationship (3-DQSAR) studies on this novel series of TST further elucidated the structure-activity relationship (SAR). The results suggested the great potential of TSTs as a novel class of NNRTIs with antiviral efficacy and a good resistance profile. (C) 2014 Elsevier Masson SAS. All rights reserved.