(2E,4E)-5-(4-methoxyphenyl)penta-2,4-dienoic acid | 50667-94-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2E,4E)-5-(4-methoxyphenyl)penta-2,4-dienoic acid
• 英文别名: 5--2,4-pentadiensaeure；5-(4-Methoxyphenyl)-2.4-pentadiensaeure；5-(4-Methoxyphenyl)penta-2,4-dienoic acid
• CAS: 50667-94-2
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: UODHHVJEXWSPFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E,4E)-5-(4-methoxyphenyl)penta-2,4-dienoic acid 在 吡啶 、 四(三苯基膦)钯 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以71%的产率得到(E)-1-(buta-1,3-diene-1-yl)-4-methoxybenzene
  参考文献：
  名称：

  钯催化多烯酸的化学选择性原羧化

  摘要：

  提出了首先钯催化的多烯酸的化学选择性原脱羧以良好的收率得到所需的多烯的条件。反应在温和的条件下使用Pd（0）或Pd（II）催化剂进行，并能耐受各种芳基和脂肪族取代。反应的独特方面包括需要膦，水和与羧酸相邻的多烯。

  DOI：

  10.1021/acs.orglett.8b03016
• 作为产物：
  描述：

  4-甲氧基肉桂醛 、 methyl 4-(triphenylphosphino)crotonate 在 lithium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以75%的产率得到(2E,4E)-5-(4-methoxyphenyl)penta-2,4-dienoic acid
  参考文献：
  名称：

  钯催化多烯酸的化学选择性原羧化

  摘要：

  提出了首先钯催化的多烯酸的化学选择性原脱羧以良好的收率得到所需的多烯的条件。反应在温和的条件下使用Pd（0）或Pd（II）催化剂进行，并能耐受各种芳基和脂肪族取代。反应的独特方面包括需要膦，水和与羧酸相邻的多烯。

  DOI：

  10.1021/acs.orglett.8b03016

文献信息

• Carbamic acid compounds comprising an amide linkage as hdac inhibitors
  申请人：——

  公开号：US20040092598A1

  公开（公告）日：2004-05-13

  This invention pertains to certain active carbamic acid compounds which inhibit HDAC activity and which have the formula (1) wherein: A is an aryl group; Q1 is an aryl leader group having a backbone of at least 2 carbon atoms; J is an amide linkage selected from: —NR1C(═O)—and —C(═O)NR1—; R1 is an amido substituent; and, Q2 is an acid leader group; and pharmaceutically acceptable salts, solvates, amides, esters, ethers, chemically protected forms, and prodrugs thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit HDAC, and, e.g., to inhibit proliferative conditions, such as cancer and psoriasis.

  这项发明涉及抑制HDAC活性的某些活性碳酸酰胺化合物，其化学式为（1），其中：A是芳基；Q1是至少有2个碳原子骨架的芳基前导基团；J是选择自以下的酰胺键：—NR1C(═O)—和—C(═O)NR1—；R1是酰胺取代基；Q2是酸前导基团；以及其药学上可接受的盐、溶剂化合物、酰胺、酯、醚、化学保护形式和前药。本发明还涉及包含这种化合物的药物组合物，以及在体外和体内使用这种化合物和组合物来抑制HDAC，例如，抑制增殖性疾病，如癌症和牛皮癣。
• Novel substituted aryl alkenoic acid heterocyclic amides
  申请人：Taneja Chandra Subhash

  公开号：US20060094874A1

  公开（公告）日：2006-05-04

  The present invention relates to novel compounds possessing specific hot, pungent and spicy taste when subjected to direct pungency evaluation, which may be useful as food additives and anti-oxidants, however the said compounds do not add to any nutritional value but the synthesised compounds can possess useful pharmacological properties which is expected to find application in new test models for the development of anti-inflammatory drugs, bioavailability enhancers and for the study of hepatic drug metabolising mechanism; also relates to a process for preparing the said compounds.

  本发明涉及一种新型化合物，当直接进行辛辣度评估时，具有特定的热辣、刺激和辛辣的口感，可用作食品添加剂和抗氧化剂，但该化合物不会增加任何营养价值，但合成的化合物可以具有有用的药理学性质，预计可在新的测试模型中应用于抗炎药物、生物利用度增强剂的开发和肝脏药物代谢机制的研究；同时涉及一种制备该化合物的方法。
• ARYL ALKENAMIDES DERIVATIVES AS MCP-1 ANTAGONISTS
  申请人：——

  公开号：US20020028833A1

  公开（公告）日：2002-03-07

  Aryl alkenamides derivatives of Formula I or a pharmaceutically acceptable salt thereof are novel MCP-1 antagonists and are thus useful in the treatment of inflammation, atherosclerosis, restenosis, and immune disorders such as arthritis and transplant rejection 1 V=O, S, NH or a bond; Ar can be unsubstituted or substituted benzimidazole, phenyl, biphenyl, pyridyl, naphthyl, quinoline, isoquinoline or indole; n=2-6; m=1-3; X=O (oxygen), S (sulfur), ═CH 2 , ═NH or H 2 ; R 1 and R 2 can independently be hydrogen, lower alkyl of from 1-4 carbon atoms, —(CH 2 ) n OR 6 , —(CH 2 ) n NR 3 R 4 , —(CH 2 ) n ′CONR 3 R 4 , —(CH 2 ) n ′COOR 6 , —(CH 2 ) r Ar′, where n′=0-6 r=0-4 R 3 and R 4 can independently be hydrogen, lower alkyl of from 1-4 carbon atoms, —(CH 2 ) n OR 6 , or —(CH 2 ) m —Ar′, which can be unsubstituted or substituted with up to 3 substitutents, where “Ar′” is phenyl, pyridyl, or indole; R 3 and R 4 may also be taken together to form a cyclic ring of 3-8 atoms which may also contain oxygen or the group NR 5 where R 5 can be hydrogen, lower alkyl of from 1-4 carbon atoms, cycloalkyl of from 5-12 carbon atoms, or —(CH 2 ) m -Phenyl, which can be unsubstituted or substituted with up to 3 substitutents; R 6 can be hydrogen, lower alkyl or (CH 2 ) m -Phenyl; m=1-3; R 1 and R 2 may be also taken together to form a ring of 3-8 atoms which may also contain oxygen or the group NR 5 , which ring may be substituted on one or more carbon atoms with the group NR 3 R 4 ; the subtituents are defined as: halogen, nitro, CF 3 , alkyl of from 1-12 carbon atoms; —(CH 2 ) r OR 6 —(CH 2 ) r NR 3 R 4 —(CH 2 ) r CONR 3 R 4 —(CH 2 ) r C(O)OR 6 or —(CH 2 ) r SO 2 —OR 6 ; R 7 , R 8 , R 9 and R 10 can each independently be hydrogen, lower alkyl or aryl; and R 7 and R 8 or R 9 and R 10 or X or R 2 when taken together can form a 5-7 membered ring including cycloalkyl, cycloalkenyl, aryl, or heteroaryl containing nitrogen, oxygen or sulfur.

  公式I的芳基烯酰胺衍生物或其药学上可接受的盐是新型MCP-1拮抗剂，因此在治疗炎症、动脉粥样硬化、再狭窄和免疫紊乱，如关节炎和移植排斥方面有用。其中，V=O，S，NH或键；Ar可以是未取代或取代苯并咪唑、苯基、联苯基、吡啶基、萘基、喹啉、异喹啉或吲哚；n=2-6；m=1-3；X=O（氧）、S（硫）、═CH2、═NH或H2；R1和R2可以独立地是氢、1-4碳原子的低烷基、—（CH2）nOR6、—（CH2）nNR3R4、—（CH2）n′CONR3R4、—（CH2）n′COOR6、—（CH2）rAr′，其中n=0-6，r=0-4；R3和R4可以独立地是氢、1-4碳原子的低烷基、—（CH2）nOR6或—（CH2）m—Ar′，其中“Ar′”可以是未取代或取代的苯基、吡啶基或吲哚，最多可以带有3个取代基；R3和R4也可以结合成为3-8个原子的环，该环也可以包含氧或基团NR5，其中R5可以是氢、1-4碳原子的低烷基、5-12碳原子的环烷基或—（CH2）m-苯基，最多可以带有3个取代基；R6可以是氢、低烷基或（CH2）m-苯基；m=1-3；R1和R2也可以结合成为3-8个原子的环，该环也可以包含氧或基团NR5，在其中一个或多个碳原子上取代基团NR3R4；取代基团的定义为：卤素、硝基、CF3、1-12碳原子的烷基；—（CH2）rOR6、—（CH2）rNR3R4、—（CH2）rCONR3R4、—（CH2）rC（O）OR6或—（CH2）rSO2—OR6；R7、R8、R9和R10可以各自独立地是氢、低烷基或芳基；当R7和R8或R9和R10或X或R2结合在一起时，可以形成一个包含氮、氧或硫的5-7个成员的环，包括环烷基、环烯基、芳基或杂芳基。
• CARBAMIC ACID COMPOUNDS COMPRISING AN AMIDE LINKAGE AS HDAC INHIBITORS
  申请人：Watkins Clare J.

  公开号：US20110105572A1

  公开（公告）日：2011-05-05

  This invention pertains to certain active carbamic acid compounds which inhibit HDAC activity and which have the following formula: wherein: A is a C 5-20 heteroaryl or C 5-20 carboaryl group and is optionally substituted; Q 1 is a C 2-7 alkylene group having a backbone of at least 2 carbon atoms, and is optionally substituted; J is —N(R 1 )C(═O)— or —C(═O)N(R 1 )—; R 1 is hydrogen, C 1-7 alkyl, C 3-20 heterocyclyl, or C 5-20 aryl; and, Q 2 is C 1-7 alkylene, C 5-20 arylene, C 5-20 arylene-C 1-7 alkylene, or C 1-7 alkylene-C 5-20 arylene having a backbone of at least 3 carbon atoms, and is optionally substituted; and pharmaceutically acceptable salts thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit HDAC, and, e.g., to treat proliferative conditions, such as cancer and psoriasis.

  本发明涉及某些活性碳酰胺酸化合物，其抑制HDAC活性，并具有以下公式：其中：A是C5-20杂环芳基或C5-20羰基芳基基团，并可选择性地取代；Q1是具有至少2个碳原子的C2-7烷基链，可选择性地取代；J是-N（R1）C（═O）-或-C（═O）N（R1）-；R1是氢，C1-7烷基，C3-20杂环芳基或C5-20芳基；Q2是具有至少3个碳原子的C1-7烷基链，C5-20芳基链，C5-20芳基链-C1-7烷基链，或C1-7烷基链-C5-20芳基链，并可选择性地取代；以及其药学上可接受的盐。本发明还涉及包含这种化合物的制药组合物，以及使用这种化合物和组合物在体内外抑制HDAC，例如治疗增殖性疾病，如癌症和牛皮癣。
• Carbamic acid compounds comprising an amide linkage as HDAC inhibitors
  申请人：TopoTarget UK Limited

  公开号：EP1598067A1

  公开（公告）日：2005-11-23

  This invention pertains to certain active carbamic acid compounds which inhibit HDAC activity and which have the following formula: wherein: A is an aryl group; Q1 is an aryl leader group having a backbone of at least 2 carbon atoms; J is an amide linkage selected from: -NR1C(=O)- and -C(=O)NR1-; R1 is an amido substituent; and, Q2 is an acid leader group; and pharmaceutically acceptable salts, solvates, amides, esters, ethers, chemically protected forms, and prodrugs thereof, for use in the treatment of parasitic infections, such as malaria.

  本发明涉及某些抑制 HDAC 活性的活性氨基甲酸化合物，它们具有下式： 其中A是芳基；Q1是具有至少2个碳原子骨架的芳基领导基团；J是选自-NR1C(＝O)-和-C(＝O)NR1-的酰胺连接；R1是氨基取代基；Q2是酸领导基团；及其药学上可接受的盐、溶液剂、酰胺、酯、醚、化学保护形式和原药，用于治疗寄生虫感染，如疟疾。