7-甲基喹啉-2-甲醛 | 103854-60-0

• 物质功能分类: 医药中间体 - 杂环化合物 - 喹啉类化合物
• 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
• 中文名称: 7-甲基喹啉-2-甲醛
• 英文名称: 7-methylquinoline-2-carbaldehyde
• 英文别名: 7-Methyl-chinolin-2-carbaldehyd；7-methyl-2-quinolinecarbaldehyde
• CAS: 103854-60-0
• 化学式: C₁₁H₉NO
• 分子量: 171.199
• InChiKey: ZCVBASSIVQYPAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  7-甲基喹啉-2-甲醛 在 sodium azide 、 四甲基乙二胺 、 copper(l) chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 生成 2-(5-azido-2-phenyl-2H-1,2,3-triazol-4-yl)-7-methylquinoline
  参考文献：
  名称：

  2-吡啶衍生的4-叠氮基-r1,2,3-三唑环化合成蓝光杂环

  摘要：

  使用相应的二氯二氮杂二烯作为前体，详细阐述了 2-吡啶衍生的 4-叠氮基-1,2,3-三唑的有效合成。制备的 2-吖嗪取代的二氮杂二烯与叠氮化钠的反应允许以高达 92% 的收率制备分离的目标三唑。研究了随后的热环化。分子氮的消除促进了氮烯在吖嗪氮上的环化。结果，制备了2 H -[1,2,3]三唑并[4',5':3,4]吡唑并[1,5 - a ]吡啶-5-ium-4-ides族。合成的化合物是新杂环系统的成员。此外，这些化合物是新的有吸引力的蓝色发光分子。

  DOI：

  10.1039/d1ob01084k
• 作为产物：
  描述：

  2,7-二甲基喹啉 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 以87%的产率得到7-甲基喹啉-2-甲醛
  参考文献：
  名称：

  连续的分子间还原胺化/不对称加氢：容易获得可手性调节的手性邻位二胺和N-杂环卡宾。

  摘要：

  已经开发出具有2-喹啉醛和芳族胺的高度对映选择性的铱或钌催化的分子间还原胺化/不对称氢化继电器。以高收率（高达95％）和出色的对映选择性（高达> 99％ee）获得了范围广泛的空间可调性手性N，N'-二芳基邻位二胺。所得的手性二胺很容易转化为空间受阻的手性N-杂环卡宾（NHC）前体，否则很难获得。通过将手性邻位二胺和手性NHC配体之一分别成功应用在过渡金属催化的不对称Suzuki-Miyaura交叉偶联反应和不对称开环交叉复分解中，进一步证明了这种合成方法的有效性。

  DOI：

  10.1002/anie.201909919

文献信息

• Asymmetric Ruthenium-Catalyzed Hydrogenation of Terpyridine-Type <i>N</i>-Heteroarenes: Direct Access to Chiral Tridentate Nitrogen Ligands
  作者：Chenghao Li、Yixiao Pan、Yu Feng、Yan-Mei He、Youran Liu、Qing-Hua Fan

  DOI：10.1021/acs.orglett.0c02268

  日期：2020.8.21

  first enantioselective hydrogenation of terpyridine-type N-heteroarenes has been successfully developed by using Ru(diamine) complexes as catalysts, providing partially reduced chiral pyridine-amine-type products in high yield (up to 93%) with excellent diastereo- and enantioselectivity (up to 94:6 dl/meso, > 99% ee). These pyridine-amine-type compounds can be served as a new class of chiral multidentate

  通过使用Ru（二胺）配合物作为催化剂成功开发了第一个对吡啶吡啶类N-杂芳烃的对映选择性加氢反应，以高收率（高达93％）提供了部分还原的手性吡啶-胺类产物，具有出色的非对映异构和对映选择性（最高94：6 dl /中观，> 99％ee）。这些吡啶-胺型化合物可用作新型的手性多齿氮供体配体，已成功应用于铜催化的吲哚与硝基烯烃的不对称Friedel-Crafts烷基化反应。
• 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。
• PFKFB3 INHIBITOR AND METHODS OF USE AS AN ANTI-CANCER THERAPEUTIC
  申请人：ADVANCED CANCER THERAPEUTICS, LLC

  公开号：US20150064175A1

  公开（公告）日：2015-03-05

  A novel compound, (E)-1-(pyridyn-4-yl)-3-(7-(trifluoromethyl)quinolin-2-yl)-prop-2-en-1-one, is provided herein. (E)-1-(pyridyn-4-yl)-3-(7-(trifluoromethyl)quinolin-2-yl)-prop-2-en-1-one is an inhibitor of 6-phosphofructo-2-kinase/fructose-2,6-biphosphatase 3 (PFKFB3) with surprisingly superior efficacy and pharmacodynamic properties in vitro and in vivo. Also provided are pharmaceutical compositions including the compound and methods of use of the compound in treating cancer and tumors in vivo, as well as inhibiting glycolytic flux and PFKFB3 enzymatic activity in cells.

  本文提供了一种新化合物，即(E)-1-(吡啶-4-基)-3-(7-(三氟甲基)喹啉-2-基)-丙-2-烯-1-酮。 (E)-1-(吡啶-4-基)-3-(7-(三氟甲基)喹啉-2-基)-丙-2-烯-1-酮是6-磷酸果糖-2-激酶/果糖-2,6-二磷酸酶3 (PFKFB3)的抑制剂，在体外和体内具有惊人的优越疗效和药理学特性。还提供了包括该化合物的制药组合物以及使用该化合物在体内治疗癌症和肿瘤以及抑制细胞中的糖酵解通量和PFKFB3酶活性的方法。