3-(4-氯苯基)-1-(5-氯-2-噻吩)-2-丙烯-1-酮 | 96583-49-2

• 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: 3-(4-氯苯基)-1-(5-氯-2-噻吩)-2-丙烯-1-酮
• 英文名称: 3-(4-chlorophenyl)-1-(5-chlorothien-2-yl)prop-2-en-1-one
• 英文别名: (E)-3-(4-chlorophenyl)-1-(5-chloro-thien-2-yl)-prop-2-en-1-one；(2E)-1-(4-chlorocyclopenta-1,3-dien-1-yl)-3-(4-chlorophenyl)prop-2-en-1-one；3t-(4-chloro-phenyl)-1-(5-chloro-[2]thienyl)-propenone；3t-(4-Chlor-phenyl)-1-(5-chlor-[2]thienyl)-propenon；3-(4-Chlorophenyl)-1-(5-chloro-2-thienyl)prop-2-en-1-one；(E)-3-(4-chlorophenyl)-1-(5-chlorothiophen-2-yl)prop-2-en-1-one
• CAS: 96583-49-2
• 化学式: C₁₃H₈Cl₂OS
• 分子量: 283.178
• InChiKey: NIHJQGCDODCOQA-ZZXKWVIFSA-N

物化性质

• 沸点：
  422.7±45.0 °C(Predicted)
• 密度：
  1.393±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  17
• 可旋转键数：
  3
• 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

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-(4-氯苯基)-1-(5-氯-2-噻吩)-2-丙烯-1-酮 在 四丁基硫酸氢铵 氢氧化钾 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.25h， 生成 [4-(4-Chloro-phenyl)-1-ethyl-1H-pyrrol-3-yl]-(5-chloro-thiophen-2-yl)-methanone
  参考文献：
  名称：

  The pyrrole moiety as a template for COX-1/COX-2 inhibitors

  摘要：

  Aroyl- and thiophene-substituted pyrrole derivatives have been synthesized as a new class of COX-1/COX-2 inhibitors. The inhibition of COX-1 was evaluated in a biological system using bovine PMNLs as the enzyme source, whereas LPS-stimulated human monocytes served as the enzyme source for inducible COX-2. The determination of the concentration of arachidonic acid metabolites was performed by HPLC for COX-1 and RIA for COX-2. Variation of the substitution pattern led to a series of active compounds which showed inhibition for COX-1 and COX-2. Structural requirements for the development of COX-1/COX-2 inhibitors are discussed, (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00150-1
• 作为产物：
  描述：

  2-乙酰基-5-氯噻酚 、 4-氯苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以98%的产率得到3-(4-氯苯基)-1-(5-氯-2-噻吩)-2-丙烯-1-酮
  参考文献：
  名称：

  氯化噻吩基查耳酮的探索：一类新的单胺氧化酶-B抑制剂。

  摘要：

  查尔酮已被报道是设计单胺氧化酶（MAO）抑制剂的有效支架。这种情况扩大了发现基于杂芳基查尔酮MAO抑制剂的势头。在本研究中，我们合成了一系列11个在环B对位上被不同官能团取代的氯化噻吩查尔酮衍生物，并研究了它们抑制人MAO-A和-B的能力。除了化合物（2E）-1-（4-氯环戊-1,3-二烯-1-基）-3-（4-硝基苯基）丙-2-烯-1-酮（TC7）选择性MAO-A抑制剂，所有其他衍生物均以竞争性抑制方式有效和选择性地抑制hMAO-B。最有效的化合物（2E）-1-（4-氯环戊-1 发现3-dien-1-yl）-3-（4-乙基苯基）prop-2-en-1-one（TC6）是对hMAO-B的最佳活性和更高的选择性，Ki和SI值为0.31±分别为0.02μM和16.84。当前研究中介绍的所有化合物对100μM浓度的肝细胞而言，都是74-88％的活细胞完全无毒。使用Autodock-4.2和Amber

  DOI：

  10.1016/j.ijbiomac.2016.05.110

文献信息

• Exploration of chlorinated thienyl chalcones: A new class of monoamine oxidase-B inhibitors
  作者：Bijo Mathew、Abitha Haridas、Gülberk Uçar、Ipek Baysal、Adebayo A. Adeniyi、Mahmoud E.S. Soliman、Monu Joy、Githa Elizabeth Mathew、Baskar Lakshmanan、Venkatesan Jayaprakash

  DOI：10.1016/j.ijbiomac.2016.05.110

  日期：2016.10

  for the design of monoamine oxidase (MAO) inhibitors. This scenario has amplified the momentum for the discovery of heteroaryl based chalcone MAO inhibitors. In the present study, we have synthesized a series of eleven chlorinated thienyl chalcone derivatives substituted with a different functional groups at the para- position on the ring B and investigated for their ability to inhibit human MAO-A and

  查尔酮已被报道是设计单胺氧化酶（MAO）抑制剂的有效支架。这种情况扩大了发现基于杂芳基查尔酮MAO抑制剂的势头。在本研究中，我们合成了一系列11个在环B对位上被不同官能团取代的氯化噻吩查尔酮衍生物，并研究了它们抑制人MAO-A和-B的能力。除了化合物（2E）-1-（4-氯环戊-1,3-二烯-1-基）-3-（4-硝基苯基）丙-2-烯-1-酮（TC7）选择性MAO-A抑制剂，所有其他衍生物均以竞争性抑制方式有效和选择性地抑制hMAO-B。最有效的化合物（2E）-1-（4-氯环戊-1 发现3-dien-1-yl）-3-（4-乙基苯基）prop-2-en-1-one（TC6）是对hMAO-B的最佳活性和更高的选择性，Ki和SI值为0.31±分别为0.02μM和16.84。当前研究中介绍的所有化合物对100μM浓度的肝细胞而言，都是74-88％的活细胞完全无毒。使用Autodock-4.2和Amber
• Synthesis and Biological Evaluation of the 1,5-Diarylpyrazole Class of Cyclooxygenase-2 Inhibitors:  Identification of 4-[5-(4-Methylphenyl)-3- (trifluoromethyl)-1<i>H</i>-pyrazol-1-yl]benzenesulfonamide (SC-58635, Celecoxib)
  作者：Thomas D. Penning、John J. Talley、Stephen R. Bertenshaw、Jeffery S. Carter、Paul W. Collins、Stephen Docter、Matthew J. Graneto、Len F. Lee、James W. Malecha、Julie M. Miyashiro、Roland S. Rogers、D. J. Rogier、Stella S. Yu、Gary D. Anderson、Earl G. Burton、J. Nita Cogburn、Susan A. Gregory、Carol M. Koboldt、William E. Perkins、Karen Seibert、Amy W. Veenhuizen、Yan Y. Zhang、Peter C. Isakson

  DOI：10.1021/jm960803q

  日期：1997.4.1

  A series of sulfonamide-containing 1,5-diarylpyrazole derivatives were prepared and evaluated for their ability to block cyclooxygenase-2 (COX-2) in vitro and in vivo. Extensive structure-activity relationship (SAR) work was carried out within this series, and a number of potent and selective inhibitors of COX-2 were identified. Since an early structural lead (1f, SC-236) exhibited an unacceptably long plasma half-life, a number of pyrazole analogs containing potential metabolic sites were evaluated further in vivo in an effort to identify compounds with acceptable pharmacokinetic profiles. This work led to the identification of ii (4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide, SC-58635, celecoxib), which is currently in phase III clinical trials for the treatment of rheumatoid arthritis and osteoarthritis.
• Buu-Hoi et al., Bulletin de la Societe Chimique de France, 1956, p. 1646,1648
  作者：Buu-Hoi et al.

  DOI：——

  日期：——
• [EN] CATALYTIC ASYMMETRIC SYNTHESIS OF OPTICALLY ACTIVE COMPOUNDS<br/>[FR] SYNTHESE ASYMETRIQUE CATALYTIQUE DE COMPOSES OPTIQUEMENT ACTIFS
  申请人：CHEMINOVA AS

  公开号：WO2003050105A2

  公开（公告）日：2003-06-19

  A one step catalytic asymmetric process for the synthesis of an optically active compound of formula la or lb wherein R is selected from C1-7 alkyl, C1-7 haloalkyl, C1-7 alkoxy, C1-7 haloalkoxy, halogen and hydroxy; R3 is H or C1-4 alkyl; R4 is selected from H, C1-7 alkyl, C1-7 haloalkyl, C1-7 alkoxy, COOH, CO-C1-7 alkoxy and an optionally substituted aryl or heterocycle; AR represents C1-7 alkyl, optionally substituted aryl, an optionally substituted heterocycle or AR and R4 may be bridged together forming part of a ring system; X is O or S; m is a number between 0-4; comprising the step of reacting a compound of the formula 2 with a compound of formula 3 in the presence of a catalytic amount of a chiral nitrogen containing organic compound.
• The pyrrole moiety as a template for COX-1/COX-2 inhibitors
  作者：Gerd Dannhardt、Werner Kiefer、Godehard Krämer、Sabine Maehrlein、Ulrike Nowe、Bernd Fiebich

  DOI：10.1016/s0223-5234(00)00150-1

  日期：2000.5

  Aroyl- and thiophene-substituted pyrrole derivatives have been synthesized as a new class of COX-1/COX-2 inhibitors. The inhibition of COX-1 was evaluated in a biological system using bovine PMNLs as the enzyme source, whereas LPS-stimulated human monocytes served as the enzyme source for inducible COX-2. The determination of the concentration of arachidonic acid metabolites was performed by HPLC for COX-1 and RIA for COX-2. Variation of the substitution pattern led to a series of active compounds which showed inhibition for COX-1 and COX-2. Structural requirements for the development of COX-1/COX-2 inhibitors are discussed, (C) 2000 Editions scientifiques et medicales Elsevier SAS.