(4-chlorophenyl)-(thiophen-2-yl)methanol | 40310-35-8

• 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: (4-chlorophenyl)-(thiophen-2-yl)methanol
• 英文别名: (4-chlorophenyl)-thiophen-2-yl-methanol；4-chlorophenyl(2-thienyl)methanol；(4-chloro-phenyl)-[2]thienyl-methanol；(4-Chlor-phenyl)-[2]thienyl-methanol；(4-chlorophenyl)-thiophen-2-ylmethanol
• CAS: 40310-35-8
• 化学式: C₁₁H₉ClOS
• 分子量: 224.711
• InChiKey: LJVKWISXJUROPV-UHFFFAOYSA-N

物化性质

• 熔点：
  59.5-60 °C
• 沸点：
  157-158 °C(Press: 0.3 Torr)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4-chlorophenyl)-(thiophen-2-yl)methanol 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 32.5h， 生成 2-[(4-Chlorophenyl)-thiophen-2-ylmethoxy]ethanol
  参考文献：
  名称：

  Structure-activity studies on benzhydrol-containing nipecotic acid and guvacine derivatives as potent, orally-active inhibitors of GABA uptake

  摘要：

  The introduction of lipophilic groups onto the ring nitrogen of nipecotic acid and guvacine, two known GABA uptake inhibitors, afforded potent, orally-active anticonvulsant drugs. A series of compounds is reported which explores the structure-activity relationships (SAR) in this series. Among the areas explored: side-chain SAR (aromatic-, heterocyclic-, and tricyclic-containing side chains) and modifications to the tetrahydropyridine ring. The benzhydrol ether-containing side chains afforded the most potent compounds with several exhibiting in vitro IC50 values for GABA uptake of <1 muM (including 5, Table 1; 37, 43, Table IV; and 44, Table V). Compound 44 was selected for extensive evaluation and subsequently progressed to Phase 1 clinical trials with severe adverse effects seen after single dose administration to humans.

  DOI：

  10.1021/jm00100a032
• 作为产物：
  描述：

  2-溴噻吩 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以79%的产率得到(4-chlorophenyl)-(thiophen-2-yl)methanol
  参考文献：
  名称：

  含有三芳基甲烷的噻吩作为抗结核药。

  摘要：

  由二芳基甲醇的弗瑞德-克来福特烷基化反应，然后结合氨基烷基链，合成了一系列新的含噻吩的三芳基甲烷衍生物。对它们进行了针对结核分枝杆菌H37R（v）的评估，并在体外显示其活性在3.12-12.5 microg / mL的范围内。

  DOI：

  10.1016/j.bmcl.2007.10.083

文献信息

• Histamine Antagonists. II.¹ Unsymmetrical 1,4-Disubstituted Piperazines
  作者：K. E. Hamlin、Arthur W. Weston、Francis E. Fischer、R. J. Michaels

  DOI：10.1021/ja01176a038

  日期：1949.8
• 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.
• Panda, Gautam; Parai, Maloy Kumar; Srivastava, Ajay Kumar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 8, p. 1121 - 1127
  作者：Panda, Gautam、Parai, Maloy Kumar、Srivastava, Ajay Kumar、Chaturvedi, Vinita、Manju、Sinha, Sudhir

  DOI：——

  日期：——
• Novel 1-[2-(Diarylmethoxy)ethyl]-2-methyl-5-nitroimidazoles as HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors. A Structure−Activity Relationship Investigation
  作者：Gabriella De Martino、Giuseppe La Regina、Alessandra Di Pasquali、Rino Ragno、Alberto Bergamini、Chiara Ciaprini、Anna Sinistro、Giovanni Maga、Emmanuele Crespan、Marino Artico、Romano Silvestri

  DOI：10.1021/jm050273a

  日期：2005.6.1

  1-[2-(Diarylmethoxy)ethyl]-2-methyl-5-nitroimidazoles (DAMNIs) is a novel family of HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) active at submicromolar concentration. Replacement of one phenyl ring of 1-[2-(diphenylmethoxy)ethyl]-2-methyl-5-nitroimidazole (4) with heterocyclic rings, such as 2-thienyl or 3-pyridinyl, led to novel DAMNIs with increased activity. In HIV-1 WT cell-based assay the racemic 1-2-alpha-(thiophen-2-yl)phenylmethoxylethyl}-2-methyl-5-nitroimidazole (7) (EC50 = 0.03 mu M) proved 5 times more active than compound 4. Docking experiments showed that the introduction of a chiral center would not affect the binding of both (R)-7 and (S)-7. The internal scoring function of the Autodock program calculated the same inhibition constant (K-i = 7.9 nM) for the two enantiomers. Compounds 7 (ID50 = 8.25 mu M) were found more active than efavirenz (ID50 = 25 mu M) against the viral RT carrying the K103N mutation, suggesting for these compounds a potential use in efavirenz based anti-AIDS regimens.
• Krishnaswamy, N. R.; Kumar, Ch. Siva Sai Kamana; Prasanna, S., Journal of Chemical Research, Miniprint, 1991, # 7, p. 1801 - 1830
  作者：Krishnaswamy, N. R.、Kumar, Ch. Siva Sai Kamana、Prasanna, S.

  DOI：——

  日期：——