(2-{4-[(2-methoxy-phenyl)-thiophen-2-yl-methyl]-phenoxy}ethyl)dimethyl-amine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2-{4-[(2-methoxy-phenyl)-thiophen-2-yl-methyl]-phenoxy}ethyl)dimethyl-amine
• 英文别名: 2-[4-[(2-methoxyphenyl)-thiophen-2-ylmethyl]phenoxy]-N,N-dimethylethanamine
• 化学式: C₂₂H₂₅NO₂S
• 分子量: 367.512
• InChiKey: KKRZOWNOXDKMQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  49.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-噻吩甲醛 在 硫酸 、 potassium carbonate 、 magnesium 作用下， 以 四氢呋喃 、 丙酮 、 苯 为溶剂， 反应 1.0h， 生成 (2-{4-[(2-methoxy-phenyl)-thiophen-2-yl-methyl]-phenoxy}ethyl)dimethyl-amine
  参考文献：
  名称：

  Thiophene containing trisubstituted methanes [TRSMs] as identified lead against Mycobacterium tuberculosis

  摘要：

  Triarylmethanes (TRAMs) and thiophene containing trisubstituted methanes (TRSMs) have been reported by us, having potential against Mycobacterium tuberculosis and Mycobacterium fortuitum strains, respectively. Further, extension through synthesis and biological evaluation of novel TRSMs resulted into an identified lead 36 (S006-830) [(diisopropyl-(2-{4-[(4-methoxy-phenyl)- thiophen-2-yl-methyll-phenoxy}-ethyl)-amine)] with MIC: 1.33 mg/L, non-toxic against Vero C-1008 cell line with selectivity index >10, ex vivo efficacy equivalent to first line TB drugs-isoniazid (INH), rifampicin (RFM) and pyrazinamide (PZA) in the mouse and human macrophages, and lung CFU count of 2.2 x 10(7) (approximately 15 fold lesser than untreated mice, 31 x 10(7)) with efficacies comparable to ethambutol (EMB) (1.27 x 10(7)) and PZA (1.9 x 10(7)). Further, S006-830 also showed potent bactericidal activity against multi-drug resistant and single-drug resistant clinical isolates of M. tuberculosis. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.03.036

文献信息

• Thiophene containing trisubstituted methanes [TRSMs] as identified lead against Mycobacterium tuberculosis
  作者：Priyanka Singh、Sudipta Kumar Manna、Amit Kumar Jana、Tiash Saha、Pankaj Mishra、Saurav Bera、Maloy Kumar Parai、Srinivas Lavanya Kumar M、Sankalan Mondal、Priyanka Trivedi、Vinita Chaturvedi、Shyam Singh、Sudhir Sinha、Gautam Panda

  DOI：10.1016/j.ejmech.2015.03.036

  日期：2015.5

  Triarylmethanes (TRAMs) and thiophene containing trisubstituted methanes (TRSMs) have been reported by us, having potential against Mycobacterium tuberculosis and Mycobacterium fortuitum strains, respectively. Further, extension through synthesis and biological evaluation of novel TRSMs resulted into an identified lead 36 (S006-830) [(diisopropyl-(2-4-[(4-methoxy-phenyl)- thiophen-2-yl-methyll-phenoxy}-ethyl)-amine)] with MIC: 1.33 mg/L, non-toxic against Vero C-1008 cell line with selectivity index >10, ex vivo efficacy equivalent to first line TB drugs-isoniazid (INH), rifampicin (RFM) and pyrazinamide (PZA) in the mouse and human macrophages, and lung CFU count of 2.2 x 10(7) (approximately 15 fold lesser than untreated mice, 31 x 10(7)) with efficacies comparable to ethambutol (EMB) (1.27 x 10(7)) and PZA (1.9 x 10(7)). Further, S006-830 also showed potent bactericidal activity against multi-drug resistant and single-drug resistant clinical isolates of M. tuberculosis. (C) 2015 Elsevier Masson SAS. All rights reserved.