(E)-3-(quinolin-2-yl)acrylaldehyde | 201928-74-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (E)-3-(quinolin-2-yl)acrylaldehyde
• 英文别名: (2E)-3-(Quinolin-2yl)-prop-2-enal；(E)-3-(2-quinolinyl)-2-propenal；3-(2-quinolyl)propenal；(E)-3-quinolin-2-ylprop-2-enal
• CAS: 201928-74-7
• 化学式: C₁₂H₉NO
• 分子量: 183.21
• InChiKey: DIEFKJUFJHCQEE-HWKANZROSA-N

物化性质

• 沸点：
  361.9±17.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-(quinolin-2-yl)acrylaldehyde 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以49%的产率得到(E)-3-quinol-2-ylprop-2-en-1-ol
  参考文献：
  名称：

  在 2 或 3 位被链烯基或炔基链取代的喹啉的制备

  摘要：

  摘要 由 2 位或 3 位官能化烯基或炔基链取代的喹啉分别由 2-喹醛和 3-溴喹啉有效合成。

  DOI：

  10.1081/scc-120006472
• 作为产物：
  描述：

  喹啉-2-甲醛 生成 (E)-3-(quinolin-2-yl)acrylaldehyde
  参考文献：
  名称：

  [EN] CARBAMIC ACID COMPOUNDS COMPRISING A BICYCLIC HETEROARYL GROUP AS HDAC INHIBITORS
  [FR] COMPOSES D'ACIDE CARBAMIQUE COMPRENANT UN GROUPE HETEROARYLE BICYCLIQUE UTILISES EN TANT QU'INHIBITEURS DE HDAC

  摘要：

  公开号：

  WO2004076386A3

文献信息

• Design, synthesis, and biological evaluation of 1,9-diheteroarylnona-1,3,6,8-tetraen-5-ones as a new class of anti-prostate cancer agents
  作者：Xiaojie Zhang、Rubing Wang、German Ruiz Perez、Guanglin Chen、Qiang Zhang、Shilong Zheng、Guangdi Wang、Qiao-Hong Chen

  DOI：10.1016/j.bmc.2016.08.006

  日期：2016.10

  inhibiting prostate cancer cell proliferation. It can be concluded from our data that 1,9-diarylnona-1,3,6,8-tetraen-5-one can serve as a new potential scaffold for the development of anti-prostate cancer agents and that pyridine-4-yls and quinolin-4-yl act as optimal heteroaromatic rings for the enhanced potency of this scaffold. Two of the most potent compounds, 68 and 75, effectively suppress PC-3 cell

  为了寻求更有效的化学疗法来治疗去势抵抗性前列腺癌并受到姜黄素类似物的启发，二十五个（1 E，3 E，6 E，8 E）-1,9-diarylnona-1,3,6,8通过Wittig反应，然后进行Horner-Wadsworth-Emmons反应，已成功合成了带有两个相同末端杂芳族环的-tetraen-5-ones。其中的二十三种是新化合物。WST-1细胞增殖测定法用于评估其对雄激素敏感性和雄激素敏感性人类前列腺癌细胞系的抗增殖作用。与姜黄素相比，二十五个合成化合物中有十八个具有显着改善的效能。最佳化合物78在抑制前列腺癌细胞增殖方面，β-内啡肽的活性比姜黄素高14到23倍。从我们的数据可以得出结论，1,9-二芳基壬娜-1,3,6,8-四烯基5-one可以作为开发抗前列腺癌药物和吡啶-4-基的新的潜在支架。和喹啉-4-基充当最佳杂芳环，以增强该支架的效能。两种最有效的化合物68和75通过激活细胞凋亡和将细胞周期阻滞在G
• Substituted quinolines for the treatment of protozoa and retrovirus co-infections
  申请人：Fakhfakh Mohamed

  公开号：US20050165052A1

  公开（公告）日：2005-07-28

  The invention relates to the use of quinolines having general formula (1), wherein R 1 denotes H; alkyl C 1 -C 15 ; alkenyl or alkynyl C 2 -C 15 ; —CHO; heteroaryl; alkyl C 1 -C 15 or alkenyl or alkynyl C 2 -C 7 comprising at least one substituent selected from among O, halogen, —OH, —CHO, —COOH, aryloxycarbonyl, alkyloxycarbonyl C 2 -C 8 , alkenyloxycarbonyl C 3 -C 9 , nitrile, aryl, heteroaryl, arylsulphone, alkylsulphone C 1 -C 7 , thioalkyl or aminoalkyl C 1 -C 7 ; alkenyl C 2 -C 7 bearing at least one substituent selected from among NH 2 , aleoxy C 1 -C 7 , phenoxy, cycloakyl C 3 -C 6 or heteroaryloxy, alkenyl or alkynyl C 2 -C 15 comprising at least one trialkylsilyl C 1 -C 7 ; R 2 , in position 3, 6 or 8, denotes H; halogen; —OH; —CHO; —COOH; alkyl or aleoxy C 1 -C 7 ; —NH2; alkenyl C 2 -C 7 ; or alkynyl C 2 -C 10 ; R 1 and R 2 do not both denote H. The invention is used for the preparation of a medicine to treat protozoan and retrovirus co-infections.

  本发明涉及使用通式（1）的喹啉，其中R1表示H; 烷基C1-C15; 烯基或炔基C2-C15; -CHO; 杂环芳基; 烷基C1-C15或烯基或炔基C2-C7，包括至少一种取代基，所述取代基从O，卤素，-OH，-CHO，-COOH，芳基氧羰基，烷氧羰基C2-C8，烯基氧羰基C3-C9，腈，芳基，杂环芳基，芳基磺酰基，烷基磺酰基C1-C7，硫代烷基或氨基烷基C1-C7中选择; 烯基C2-C7具有从NH2，烷氧基C1-C7，苯氧基，环烷基C3-C6或杂环氧基，烯基或炔基C2-C15包括至少一个三烷基硅基C1-C7; R2，在位置3、6或8，表示H; 卤素; -OH; -CHO; -COOH; 烷基或烷氧基C1-C7; -NH2; 烯基C2-C7; 或炔基C2-C10; R1和R2不能同时表示H。该发明用于制备治疗原虫和逆转录病毒共感染的药物。
• Carbamic acid compounds comprising a bicyclic heteroaryl group as hdac inhibitors
  申请人：Finn W Paul

  公开号：US20060079528A1

  公开（公告）日：2006-04-13

  This invention pertains to certain carbamic acid compounds of the following formula, which inhibit HDAC (histone deacetylase) activity wherein: A is independently an unsubstituted or substituted bicyclic C 9-10 heteroaryl group (e.g., quinolinyl; quinoxalinyl; benzoxazolyl; benzothiazolyl); Q is an acid leader group, and is independently an unsubstituted or substituted, saturated or unsaturated C 17 alkylene group having a backbone length of 4 or less; with the proviso that if A is unsubstituted benzothiazol-2-yl, then Q is an unsaturated group; and with the proviso that if A is unsubstituted quinolin-6-yl, then Q is unsubstituted at the a-position; and with the proviso that A is not benzimidazol-2-yl; 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 in the treatment of conditions mediated by HDAC, cancer, proliferative conditions, psoriasis, etc.

  本发明涉及以下公式的某些碳酰胺化合物，其抑制HDAC（组蛋白去乙酰化酶）活性，其中：A是独立的未取代或取代的双环C9-10杂环基团（例如，喹啉基；喹啉并咪唑基；苯并噁唑基；苯并噻唑基）；Q是酸性引导基团，且是独立的未取代或取代的饱和或不饱和C17烷基基团，其骨架长度不超过4；但前提是，如果A是未取代的苯并噻唑-2-基，则Q是不饱和基团；如果A是未取代的喹啉-6-基，则Q在α位未取代；A不能是苯并咪唑-2-基；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些化合物的制药组合物，以及在体内外使用这些化合物和组合物来抑制HDAC并治疗由HDAC介导的疾病，如癌症，增殖性疾病，牛皮癣等。
• Heteroaromatic pentadienoic acid derivatives useful as inhibitors of
  申请人：SmithKline Beecham SpA

  公开号：US06025390A1

  公开（公告）日：2000-02-15

  A compound of formula (I) or a salt thereof, or a solvate thereof, ##STR1## wherein: R.sub.1 represents an alkyl group or a substituted or unsubstituted aryl group; R.sub.2, R.sub.3 and R.sub.4 each independently represent hydrogen, alkyl, aryl or substituted aryl; R.sub.5 and R.sub.6 each independently represent hydrogen, hydroxy, amino, alkoxy, optionally substituted aryloxy, optionally substituted benzyloxy, alkylamino, dialkylamino, halo, trifluoromethyl, trifluoromethoxy, nitro, alkyl, carboxy, carbalkoxy, carbamoyl, alkylcarbamoyl, or R.sub.5 and R.sub.6 together represent methylenedioxy, carbonyldioxy or carbonyldiamino; X represents a hydroxy or an alkoxy group wherein the alkyl group may be substituted or unsubstituted or X represents a group NR.sub.S R.sub.t wherein R.sub.S and R.sub.t each independently represent hydrogen, alkyl, substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted arylalkyl, an optionally substituted heterocyclic group or an optionally substituted heterocyclylalkyl group, or R.sub.S and R.sub.t together with the nitrogen to which they are attached form a heterocyclic group; and Y represents O or S and Z represents CH, CH.dbd.CH or N; or Y represents NR.sub.7 wherein R.sub.7 represents hydrogen, hydroxy, alkanoyl, alkyl, aminoalkyl, hydroxyalkyl, carboxyalkyl, carbalkoxyalkyl, carbamoyl or aminosulphonyl and Z represents CH.dbd.CH or N; a pharmaceutical composition containing such a compound, a process for preparing such a compound and the use of such a compound in medicine.

  化合物的式子（I）或其盐，或其溶剂化物，其中：R.sub.1代表烷基或取代或未取代的芳基；R.sub.2，R.sub.3和R.sub.4各自独立地代表氢，烷基，芳基或取代的芳基；R.sub.5和R.sub.6各自独立地代表氢，羟基，氨基，烷氧基，可选取代的芳氧基，可选取代的苄氧基，烷基氨基，二烷基氨基，卤素，三氟甲基，三氟甲氧基，硝基，烷基，羧基，羧烷氧基，氨基甲酰基，烷基氨甲酰基，或R.sub.5和R.sub.6共同代表亚甲二氧基，羰基二氧基或羰基二氨基；X代表羟基或烷氧基，其中烷基可以取代或未取代，或X代表一个NR.sub.S R.sub.t基团，其中R.sub.S和R.sub.t各自独立地代表氢，烷基，取代的烷基，可选取代的烯基，可选取代的芳基，可选取代的芳基烷基，可选取代的杂环基或可选取代的杂环基烷基，或R.sub.S和R.sub.t与它们连接的氮共同形成一个杂环基团；Y代表O或S，Z代表CH，CH.dbd.CH或N；或Y代表NR.sub.7，其中R.sub.7代表氢，羟基，烷酰基，烷基，氨基烷基，羟基烷基，羧基烷基，羧烷氧基烷基，氨基甲酰基或氨基磺酰基，Z代表CH.dbd.CH或N；包含这种化合物的药物组合物，制备这种化合物的过程以及这种化合物在医学上的用途。
• CARBAMIC ACID COMPOUNDS COMPRISING A BICYCLIC HETEROARYL GROUP AS HDAC INHIBITORS
  申请人：FINN Paul W.

  公开号：US20100093743A1

  公开（公告）日：2010-04-15

  This invention pertains to certain carbamic acid compounds of the following formula, which inhibit HDAC (histone deacetylase) activity wherein: A is independently an unsubstituted or substituted bicyclic C 9-10 heteroaryl group (e.g., quinolinyl; quinoxalinyl; benzoxazolyl; benzothiazolyl); Q is an acid leader group, and is independently an unsubstituted or substituted, saturated or unsaturated C 1 7 alkylene group having a backbone length of 4 or less; with the proviso that if A is unsubstituted benzothiazol-2-yl, then Q is an unsaturated group; and with the proviso that if A is unsubstituted quinolin-6-yl, then Q is unsubstituted at the α-position; and with the proviso that A is not benzimidazol-2-yl; 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 in the treatment of conditions mediated by HDAC, cancer, proliferative conditions, psoriasis, etc.

  本发明涉及以下式的某些碳酰胺类化合物，其抑制HDAC（组蛋白去乙酰化酶）活性，其中：A是独立的未取代或取代的双环C9-10杂环基团（例如，喹啉基；喹啉氧基基；苯并噁唑基；苯并噻唑基）；Q是酸性引导基团，且是独立的未取代或取代的饱和或不饱和的C1 7烷基基团，其骨架长度为4或更短；但是，如果A是未取代的苯并噻唑-2-基，则Q是不饱和基团；如果A是未取代的喹啉-6-基，则Q在α-位置未取代；且A不是苯并咪唑-2-基；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些化合物的制药组合物，以及这些化合物和组合物在体内外抑制HDAC和治疗由HDAC介导的疾病，如癌症、增殖性疾病、牛皮癣等方面的用途。