3-喹噁啉-2-丙烯酸 | 1593-24-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 3-喹噁啉-2-丙烯酸
• 中文别名: 3-喹喔啉-2-基-丙烯酸
• 英文名称: 2-<2-Carboxy-vinyl>-chinoxalin
• 英文别名: β-2-Chinoxalinyl-propensaeure；3-quinoxalin-2-yl-acrylic acid；3t-quinoxalin-2-yl-acrylic acid；3t-Chinoxalin-2-yl-acrylsaeure；(E)-3-(2-quinoxalinyl)-2-propenoic acid；(E)-3-quinoxalin-2-ylprop-2-enoic acid
• CAS: 1593-24-4
• 化学式: C₁₁H₈N₂O₂
• mdl: MFCD03002884
• 分子量: 200.197
• InChiKey: QJNZVVWLYVQBPQ-AATRIKPKSA-N

物化性质

• 熔点：
  219-220 °C (decomp)
• 沸点：
  386.7±27.0 °C(Predicted)
• 密度：
  1.374±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 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：
  63.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-喹噁啉-2-丙烯酸 在 sodium hydroxide 、 镍 作用下， 生成 3-喹噁啉-2-丙酸
  参考文献：
  名称：

  The Synthesis of Some β-Aminoethyldiazines as Histamine Analogs

  摘要：

  DOI：

  10.1021/ja01164a061
• 作为产物：
  描述：

  1,1,1-trichloro-3-quinoxalin-2-yl-propan-2-ol 在 氢氧化钾 作用下， 生成 3-喹噁啉-2-丙烯酸
  参考文献：
  名称：

  Ried; Keller, Chemische Berichte, 1956, vol. 89, p. 2578,2582

  摘要：

  DOI：

文献信息

• [EN] INDAZOLE DERIVATIVES AS αV INTEGRIN ANTAGONISTS<br/>[FR] DÉRIVÉS D'INDAZOLE EN TANT QU'ANTAGONISTES DE L'INTÉGRINE αV
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2018089357A1

  公开（公告）日：2018-05-17

  The present invention provides compounds of Formula (Ia) or (Ib): or stereoisomers, tautomers, or pharmaceutically acceptable salts or solvates thereof, wherein all the variables are as defined herein. These compounds are antagonists to αV- containing integrins. This invention also relates to pharmaceutical compositions comprising these compounds and methods of treating a disease, disorder, or condition associated with dysregulation of αV-containing integrins, such as pathological fibrosis, transplant rejection, cancer, osteoporosis, and inflammatory disorders, by using the compounds and pharmaceutical compositions.

  本发明提供了式（Ia）或（Ib）的化合物：或其立体异构体、互变异构体或药学上可接受的盐或溶剂，其中所有变量如本文所定义。这些化合物是αV-含有整合素的拮抗剂。本发明还涉及包括这些化合物的药物组合物以及使用这些化合物和药物组合物治疗与αV-含有整合素失调相关的疾病、紊乱或状况的方法，如病理性纤维化、移植排斥、癌症、骨质疏松症和炎症性疾病。
• 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。
• 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。
• Substituted 2,3-Dihydrobenzofuranyl Compounds And Uses Thereof
  申请人：KARYOPHARM THERAPEUTICS INC.

  公开号：US20160221994A1

  公开（公告）日：2016-08-04

  The invention generally relates to substituted 2,3-dihydrobenzofuranyl compounds, and more particularly to a compound represented by Structural Formula (I), or a pharmaceutically acceptable salt thereof, wherein the variables are as defined and described herein. The invention also includes the synthesis and use of a compound of Structural Formula (I), or a pharmaceutically acceptable salt or composition thereof, e.g., in the treatment of cancer (e.g., mantle cell lymphoma), and other diseases and disorders.

  本发明通常涉及取代的2,3-二氢苯并呋喃基化合物，更具体地涉及由结构式（I）表示的化合物，或其药学上可接受的盐，在此变量的定义和描述中。本发明还包括合成和使用结构式（I）的化合物，或其药学上可接受的盐或组合物，例如在治疗癌症（例如曼托细胞淋巴瘤）和其他疾病和障碍中。
• Discovery of a novel piperlongumine analogue as a microtubule polymerization inhibitor with potent anti-angiogenic and anti-metastatic efficacy
  作者：Jinling Qin、Hongliang Li、Xuan Wang、Yixin Zhang、Yongtao Duan、Yongfang Yao、Hua Yang、Moran Sun

  DOI：10.1016/j.ejmech.2022.114738

  日期：2022.12

  with an IC50 value of 5.8 μM. Further studies elucidated that II-14b showed antitumor activities through multiple mechanisms, including the pruduction of abundant ROS, the dissipation of mitochondrial membrane potential, the accumulation of DNA double-strand breaks, and the induction of cell cycle in G2/M phase. More importantly, we have observed that it possesses potential anti-angiogenesis capabilities

  为了发现同时作用于微管蛋白和血管生成的抗癌药物，我们设计并合成了两个系列的荜茇(PL)衍生物，通过用各种苯并杂环(系列II)取代苯基或将C7-C8烯烃环化成芳香杂环（系列 I）。大多数新化合物对六种癌细胞系表现出比母体药物 PL 更好的抗增殖活性。化合物II-14b在这两个系列中对癌细胞具有最佳的细胞毒性，同时对正常人体细胞的细胞毒性相对较低，对耐药细胞的细胞毒性较高。它破坏细胞微管网络并抑制微管蛋白组装，IC 50值为 5.8 μM。进一步的研究表明， II-14b通过多种机制表现出抗肿瘤活性，包括产生丰富的ROS、耗散线粒体膜电位、积累DNA双链断裂以及诱导细胞周期进入G2/M期。更重要的是，我们观察到它具有潜在的抗血管生成能力，包括在体外和体内抑制HUVEC细胞迁移、侵袭和内皮管形成。体内评估表明II-14b抑制斑马鱼 MGC-803 异种移植肿瘤的生长和转移。这些研究结果表明II-14b是一种高效、无毒的抗肿瘤药物。