5-bromo-6-methoxyquinoline-2-carboxaldehyde | 754190-60-8

• 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: 5-bromo-6-methoxyquinoline-2-carboxaldehyde
• 英文别名: 5-bromo-6-methoxy-2-quinolinecarbaldehyde；5-bromo-6-methoxy-2-quinolinecarboxaldehyde；5-bromo-6-methoxyquinoline-2-carbaldehyde
• CAS: 754190-60-8
• 化学式: C₁₁H₈BrNO₂
• 分子量: 266.094
• InChiKey: BWSNSGXFENOYMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-6-methoxyquinoline-2-carboxaldehyde 在 四(三苯基膦)钯 potassium dichromate 、 重铬酸吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 64.17h， 生成 5-(4-hydroxyphenyl)-6-methoxy-2-(3',4',5'-trimethoxybenzoyl)quinoline
  参考文献：
  名称：

  AROYLQUINOLINE COMPOUNDS

  摘要：

  提供了一系列含有结构式（I）的硝基杂环衍生物。在结构式（I）中，P、Q和R1至R8在说明书中有定义。本发明揭示的衍生物具有抑制微管聚合的特性，并可使用合适的药用载体治疗癌症和其他与微管聚合有关的疾病。

  公开号：

  US20110275643A1
• 作为产物：
  描述：

  6-甲氧基-2-甲基喹啉 在 selenium(IV) oxide 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 对二甲苯 、 乙腈 为溶剂， 反应 12.0h， 生成 5-bromo-6-methoxyquinoline-2-carboxaldehyde
  参考文献：
  名称：

  AROYLQUINOLINE COMPOUNDS

  摘要：

  提供了一系列含有结构式（I）的硝基杂环衍生物。在结构式（I）中，P、Q和R1至R8在说明书中有定义。本发明揭示的衍生物具有抑制微管聚合的特性，并可使用合适的药用载体治疗癌症和其他与微管聚合有关的疾病。

  公开号：

  US20110275643A1

文献信息

• 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。
• Carbamic acid compounds comprising a bicyclic heteroaryl group as HDAC inhibitors
  申请人：Topotarget UK Limited

  公开号：US08071620B2

  公开（公告）日：2011-12-06

  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 C9-10heteroaryl group (e.g., quinolinyl; quinoxalinyl; benzoxazolyl; benzothiazolyl); Q is an acid leader group, and is independently an unsubstituted or substituted, saturated or unsaturated C1-7alkylene 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.

  本发明涉及以下公式的某些碳酸酰化合物，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C9-10杂环芳基基团（例如，喹啉基；喹啉啉基；苯并噁唑基；苯并噻唑基）；Q是酸性引导基团，且独立地是未取代或取代的，饱和或不饱和的C1-7烷基基团，具有4个或更少的骨架长度；但如果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；并且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药物组成物，以及在体内外使用这些化合物和组合物来抑制HDAC，并用于治疗由HDAC介导的疾病，如癌症、增殖性疾病、牛皮癣等。
• 5-Amino-2-aroylquinolines as Highly Potent Tubulin Polymerization Inhibitors. Part 2. The Impact of Bridging Groups at Position C-2
  作者：Hsueh-Yun Lee、Jang-Yang Chang、Chih-Ying Nien、Ching-Chuan Kuo、Kuang-Hsing Shih、Chun-Hsein Wu、Chi-Yen Chang、Wen-Yang Lai、Jing-Ping Liou

  DOI：10.1021/jm201031f

  日期：2011.12.22

  A variety of studies on the modification of combretastatin A-4 triggered our interest in the impact of the linkers between the 3,4,5-trimethoxyphenyl ring and 5-amino-6-methoxyquinoline on biological activity. The replacement of the carbonyl group with bond, amine, ether, sulfide, and sulfone groups was evaluated in this study. The results showed that compounds 14 and 15 containing sulfide and sulfone groups between the 3,4,5-trimethoxyphenyl ring (A-ring) and 5-amino-6-methoxyquinoline exhibited substantial antiproliferative activity against KB, HT29, and MKN45 cells with mean IC50 values of 42 and 12 nM, respectively. 15 inhibited the tubulin polymerization with an IC50 value of 2.0 mu M, similar to that with CA4. The continued work on the C-5 substituents of 3',4',5'-trimethoxybenzoyl-6-methoxyquinoline derivatives demonstrated that compound 7 possessing OH at C-5 exhibited excellent antiproliferative activity with mean IC50 values of 3.4 nM and microtubule destabilizing potency with an IC50 of 1.5 mu M, comparable to that of CA4 (IC50 = 1.9 mu M). It also exhibited substantial vascular disrupting effects. Compounds 7 and 15 exhibited significant efficacy against MDR/MRP-related drug-resistant cell lines (KB-vin10, KB-S15, and KB-7D) with mean IC50 values of 6.7 and 2.6 nM, respectively.
• [EN] CARBAMIC ACID COMPOUNDS COMPRISING A BICYCLIC HETEROARYL GROUP AS HDAC INHIBITORS<br/>[FR] COMPOSES D'ACIDE CARBAMIQUE COMPRENANT UN GROUPE HETEROARYLE BICYCLIQUE UTILISES EN TANT QU'INHIBITEURS DE HDAC
  申请人：TOPOTARGET UK LTD

  公开号：WO2004076386A3

  公开（公告）日：2004-10-28