5-(2-chlorophenyl)thiophene-2-carbaldehyde | 356570-11-1

• 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: 5-(2-chlorophenyl)thiophene-2-carbaldehyde
• CAS: 356570-11-1
• 化学式: C₁₁H₇ClOS
• mdl: MFCD01918086
• 分子量: 222.695
• InChiKey: LOEKFPAEXOYFGC-UHFFFAOYSA-N

物化性质

• 沸点：
  350.8±32.0 °C(Predicted)
• 密度：
  1.327±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(2-chlorophenyl)thiophene-2-carbaldehyde 在 lithium hydroxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 2-Benzoylamino-3-[5-(2-chloro-phenyl)-thiophen-2-yl]-acrylic acid
  参考文献：
  名称：

  Inhibitors of HCV NS5B polymerase. Part 1: Evaluation of the southern region of (2Z)-2-(benzoylamino)-3-(5-phenyl-2-furyl)acrylic acid

  摘要：

  A novel series of nonnucleoside HCV NS5B polymerase inhibitors were prepared from (2Z)-2-(benzoylamino)-3-(5-phenyl-2-furyl)acrylic acid, a high throughput screening lead. SAR studies combined with structure based drug design focusing on the southern heterobiaryl region of the template led to the synthesis of several potent and orally bioavailable lead compounds. X-ray crystallography studies were also performed to understand the interaction of these inhibitors with HCV NS5B polymerase.

  DOI：

  10.1016/j.bmcl.2005.03.066
• 作为产物：
  描述：

  5-溴噻吩-2-甲醛 、 2-氯苯基硼酸 在 palladium diacetate 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 水 为溶剂， 反应 16.0h， 生成 5-(2-chlorophenyl)thiophene-2-carbaldehyde
  参考文献：
  名称：

  Inhibitors of HCV NS5B polymerase. Part 1: Evaluation of the southern region of (2Z)-2-(benzoylamino)-3-(5-phenyl-2-furyl)acrylic acid

  摘要：

  A novel series of nonnucleoside HCV NS5B polymerase inhibitors were prepared from (2Z)-2-(benzoylamino)-3-(5-phenyl-2-furyl)acrylic acid, a high throughput screening lead. SAR studies combined with structure based drug design focusing on the southern heterobiaryl region of the template led to the synthesis of several potent and orally bioavailable lead compounds. X-ray crystallography studies were also performed to understand the interaction of these inhibitors with HCV NS5B polymerase.

  DOI：

  10.1016/j.bmcl.2005.03.066

文献信息

• Aryl-link-aryl substituted thiazolidine-dione and oxazolidine-dione as sodium channel blockers
  申请人：Ayer B. Michelle

  公开号：US20050165072A1

  公开（公告）日：2005-07-28

  Aryl-link-aryl thiazolidine-dione and aryl-link-aryl oxazolidine-dione compounds are sodium channel blockers; pharmaceutical compositions that include an effective amount of the aryl-link-aryl thiazolidine-dione and aryl-link-aryl oxazolidine-dione compounds and a pharmaceutically acceptable carrier, and a method of treatment of acute pain, chronic pain, visceral pain, inflammatory pain, or neuropathic pain, as well as initable bowel syndrome, Cnohns disease, epilepsy, partial and generalized tonic seizures, multiple sclerosis, bipolar depression, and tachy-arrhythmias by the administration of an effective amount of aryl-link-aryl thiazolidine-dione and aryl-link-aryl oxazolidine-dione compounds are described.

  Aryl-link-aryl噻唑烷二酮和aryl-link-aryl噁唑烷二酮化合物是钠通道阻滞剂；其中包括有效量的aryl-link-aryl噻唑烷二酮和aryl-link-aryl噁唑烷二酮化合物以及药学上可接受的载体的制药组合物，以及通过给予有效量的aryl-link-aryl噻唑烷二酮和aryl-link-aryl噁唑烷二酮化合物的方法治疗急性疼痛、慢性疼痛、内脏疼痛、炎症性疼痛或神经病性疼痛，以及易激性肠综合症、克罗恩病、癫痫、部分和全身强直性发作、多发性硬化、双相抑郁症和快速心律失常。
• Exploration of a Series of 5-Arylidene-2-thioxoimidazolidin-4-ones as Inhibitors of the Cytolytic Protein Perforin
  作者：Julie A. Spicer、Gersande Lena、Dani M. Lyons、Kristiina M. Huttunen、Christian K. Miller、Patrick D. O’Connor、Matthew Bull、Nuala Helsby、Stephen M. F. Jamieson、William A. Denny、Annette Ciccone、Kylie A. Browne、Jamie A. Lopez、Jesse Rudd-Schmidt、Ilia Voskoboinik、Joseph A. Trapani

  DOI：10.1021/jm401604x

  日期：2013.12.12

  A series of novel 5-arylidene-2-thioxoimidazolidin-4-ones were investigated as inhibitors of the lymphocyte-expressed pore-forming protein perform. Structure activity relationships were explored through variation of an isoindolinone or 3,4-dihydroisoquinolinone subunit on a fixed 2-thioxoimidazolidin-4-one/thiophene core. The ability of the resulting compounds to inhibit the lytic activity of both isolated perform protein and perforin delivered in situ by natural killer cells was determined. A number of compounds showed excellent activity at concentrations that were nontoxic to the killer cells, and several were a significant improvement on previous classes of inhibitors, being substantially more potent and soluble. Representative examples showed rapid and reversible binding to immobilized mouse perforin at low concentrations (<= 2.5 mu M) by surface plasmon resonance and prevented formation of perforin pores in target cells despite effective target cell engagement, as determined by calcium influx studies. Mouse PK studies of two analogues showed T-1/2 values of 1.1-1.2 h (dose of 5 mg/kg iv) and MTDs of 60-80 mg/kg (ip).
• EP1501509A4
  申请人：——

  公开号：EP1501509A4

  公开（公告）日：2009-07-15
• ARYL-LINK-ARYL SUBSTITUTED THIAZOLIDINE-DIONE AND OXAZOLIDINE-DIONE AS SODIUM CHANNEL BLOCKERS
  申请人：Merck & Co., Inc.

  公开号：EP1501509A2

  公开（公告）日：2005-02-02
• US7348348B2
  申请人：——

  公开号：US7348348B2

  公开（公告）日：2008-03-25