2-[2-溴甲基苯基]噻吩 | 791078-04-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[2-溴甲基苯基]噻吩
• 中文别名: 2-[2-(溴甲基)苯基]噻吩
• 英文名称: 2-(2'-thiophene)benzyl bromide
• 英文别名: 2-[2-(bromomethyl)phenyl]thiophene；2-(bromomethylphenyl)thiophene
• CAS: 791078-04-1
• 化学式: C₁₁H₉BrS
• 分子量: 253.162
• InChiKey: IJNVNLWIQXMBPA-UHFFFAOYSA-N

物化性质

• 沸点：
  342.5±30.0 °C(Predicted)
• 密度：
  1.457±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 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：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  C
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  6-((4-nitrobenzyl)thio)-9H-purine 、 2-[2-溴甲基苯基]噻吩 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.08h， 以36%的产率得到6-(4-Nitro-benzylsulfanyl)-9-(2-thiophen-2-yl-benzyl)-9H-purine
  参考文献：
  名称：

  Inhibition of Nucleoside Transport by New Analogues of 4-Nitrobenzylthioinosine:  Replacement of the Ribose Moiety by Substituted Benzyl Groups

  摘要：

  4-Nitrobenzylthioinosine (NBTI, 1) is a well-known inhibitor for the nucleoside transport protein ENT1. However, its highly polar nature is unfavorable for oral absorption and/or penetration into the CNS. In the search for compounds with lower polarity than NBTI we replaced its ribose moiety by substituted benzyl groups. Halogen, hydroxyl, (trifluoro)methyl(-oxy), nitro, and amine functionalities were among the substituents at the benzyl group. In general, substitution of the benzyl group resulted in a lower affinity for ENT1. Only 2-hydroxyl substitution showed a higher affinity. Most likely this is the result of hydrogen bonding. Substitution at the 2-position of the benzyl group with aryl groups was also addressed. Compared to parent compound carrying a 2-phenylbenzyl group, all synthesized analogues gave higher affinities. Introduction of fluoro, trifluoromethyl, methoxy, and hydroxyl groups at the phenyl group clearly showed that addition to the 4-position was preferable. Despite the highly different character of a ribose and a benzyl group, K-i values in the low nanomolar range were obtained for the benzyl-substituted derivatives. Compound 35, LUF5919, and compound 60, LUF5929, displayed the highest affinity (K-i = 39 nM for both compounds), having a polar surface area of 101 Angstrom(2) and 85 Angstrom(2), respectively.

  DOI：

  10.1021/jm049735v
• 作为产物：
  描述：

  2-(2-methylphenyl)thiophene 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 40.0h， 生成 2-[2-溴甲基苯基]噻吩
  参考文献：
  名称：

  Inhibition of Nucleoside Transport by New Analogues of 4-Nitrobenzylthioinosine:  Replacement of the Ribose Moiety by Substituted Benzyl Groups

  摘要：

  4-Nitrobenzylthioinosine (NBTI, 1) is a well-known inhibitor for the nucleoside transport protein ENT1. However, its highly polar nature is unfavorable for oral absorption and/or penetration into the CNS. In the search for compounds with lower polarity than NBTI we replaced its ribose moiety by substituted benzyl groups. Halogen, hydroxyl, (trifluoro)methyl(-oxy), nitro, and amine functionalities were among the substituents at the benzyl group. In general, substitution of the benzyl group resulted in a lower affinity for ENT1. Only 2-hydroxyl substitution showed a higher affinity. Most likely this is the result of hydrogen bonding. Substitution at the 2-position of the benzyl group with aryl groups was also addressed. Compared to parent compound carrying a 2-phenylbenzyl group, all synthesized analogues gave higher affinities. Introduction of fluoro, trifluoromethyl, methoxy, and hydroxyl groups at the phenyl group clearly showed that addition to the 4-position was preferable. Despite the highly different character of a ribose and a benzyl group, K-i values in the low nanomolar range were obtained for the benzyl-substituted derivatives. Compound 35, LUF5919, and compound 60, LUF5929, displayed the highest affinity (K-i = 39 nM for both compounds), having a polar surface area of 101 Angstrom(2) and 85 Angstrom(2), respectively.

  DOI：

  10.1021/jm049735v

文献信息

• Angiotensin II antagonists incorporating a substituted thiophene or furan
  申请人：MERCK & CO. INC.

  公开号：EP0510812A1

  公开（公告）日：1992-10-28

  Substituted heterocycles attached through a methylene bridge to novel substituted phenyl thiophene or phenyl furan derivative of the Formula I are useful as angiotensin II antagonists.

  通过亚甲基桥连接到式 I 的新型取代苯基噻吩或苯基呋喃衍生物上的取代杂环可用作血管紧张素 II 拮抗剂。
• Discovery of 2-[5-(4-Fluorophenylcarbamoyl)pyridin-2-ylsulfanylmethyl]phenylboronic Acid (SX-517): Noncompetitive Boronic Acid Antagonist of CXCR1 and CXCR2
  作者：Dean Y. Maeda、Angela M. Peck、Aaron D. Schuler、Mark T. Quinn、Liliya N. Kirpotina、Winston N. Wicomb、Guo-Huang Fan、John A. Zebala

  DOI：10.1021/jm500827t

  日期：2014.10.23

  The G protein-coupled chemokine receptors CXCR1 and CXCR2 play key roles in inflammatory diseases and carcinogenesis. In inflammation, they activate and recruit polymorphonuclear cells (PMNs) through binding of the chemokines CXCL1 (CXCR1) and CXCL8 (CXCR1 and CXCR2). Structure-activity studies that examined the effect of a novel series of S-substituted 6-mercapto-N-phenyl-nicotinamides on CXCL1-stimulated Ca2+ flux in whole human PMNs led to the discovery of 2-[5-(4-fluorophenylcarbamoyl)pyridin-2-ylsulfanylmethyl]phenylboronic acid (SX-517), a potent noncompetitive boronic acid CXCR1/2 antagonist. SX-517 inhibited CXCL1-induced Ca2+ flux (IC50 = 38 nM) in human PMNs but had no effect on the Ca2+ flux induced by C5a, fMLF, or PAF. In recombinant HEK293 cells that stably expressed CXCR2, SX-517 antagonized CXCL8-induced [S-35]GTP?S binding (IC50 = 60 nM) and ERK1/2 phosphorylation. Inhibition was noncompetitive, with SX-517 unable to compete the binding of [I-125]-CXCL8 to CXCR2 membranes. SX-517 (0.2 mg/kg iv) significantly inhibited inflammation in an in vivo murine model. SX-517 is the first reported boronic acid chemokine antagonist and represents a novel pharmacophore for CXCR1/2 antagonism.
• PYRIDONE DERIVATIVES AND THEIR USE AS KINASE INHIBITORS
  申请人：SELVITA S.A.ó

  公开号：US20180305331A1

  公开（公告）日：2018-10-25

  Disclosed in the present application is a compound of formula (I) as defined herein as well as a pharmaceutical composition comprising said compound. Further disclosed in the present application is the use of such pharmaceutical compositions for treating diseases, namely inter alia for use in the treatment of cancer, metabolic, inflammatory, autoimmune and viral diseases. The compounds disclosed herein are inhibitors of MNK1 and/or MNK2 kinases.
• US4426524A
  申请人：——

  公开号：US4426524A

  公开（公告）日：1984-01-17
• US5177074A
  申请人：——

  公开号：US5177074A

  公开（公告）日：1993-01-05