6-羟基-2-甲基吡啶-3-羧酸 | 66909-37-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 6-羟基-2-甲基吡啶-3-羧酸
• 中文别名: 4-(2,4-二甲氧基苯基)-1,4,5,6-四氢-2-甲基-6-氧代-3-吡啶羧酸
• 英文名称: 2-Hydroxy-6-methyl-5-pyridincarboxylsaeure
• 英文别名: 6-hydroxy-2-methyl-nicotinic acid；6-Hydroxy-2-methyl-nicotinsaeure；6-Hydroxy-2-methylnicotinic acid；2-methyl-6-oxo-1H-pyridine-3-carboxylic acid
• CAS: 66909-37-3
• 化学式: C₇H₇NO₃
• mdl: MFCD09881218
• 分子量: 153.137
• InChiKey: AHBQPFRWFDTJNE-UHFFFAOYSA-N

物化性质

• 熔点：
  153 °C (decomp)(Solv: water (7732-18-5))
• 沸点：
  370.4±42.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090
• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319

反应信息

• 作为反应物：
  描述：

  6-羟基-2-甲基吡啶-3-羧酸 在 四(三苯基膦)钯 、 四丁基溴化铵 、 potassium carbonate 、 三乙胺 、 乙酰氯 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 144.0h， 生成 methyl 2-methyl-6-phenyl-3-pyridinecarboxylate
  参考文献：
  名称：

  Biaryl substituted alkylboronate esters as thrombin inhibitors

  摘要：

  Thrombin is a serine protease that plays an important role in the blood coagulation cascade, and is a target enzyme for new therapeutic agents. Ac-(D)-Phe-Pro-boroArg-OH (DuP714) was found to be a highly effective thrombin inhibitor. In order to reduce the peptidic nature of DuP 714, we have designed a series of novel biaryl substituted alkylboronate esters as potent thrombin inhibitors. The most potent compounds have subnanomolar affinity for thrombin. (C) 1997 The DuPont Merck Pharmaceutical Company. Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00254-0
• 作为产物：
  描述：

  2-甲基-6-氧代-1-2,6-二氢-3-羧酸乙酯 在 sodium hydroxide 作用下， 反应 3.0h， 以74%的产率得到6-羟基-2-甲基吡啶-3-羧酸
  参考文献：
  名称：

  Synthesis of 1,4-dihydro-2-methyl-4-oxo-nicotinic acid: Ochiai's route failed

  摘要：

  The synthesis of 1,4-dihydro-2-methyl- and 1,4-dihydro-1,2-dimethyl-4-oxo-nicotinic acids was accomplished following a route other than Ochiai's procedure, which yielded the isomer 1,6-dihydro-2-methyl-6-oxo-nicotinic acid ethyl ester, and not the 4-oxo-derivative, as reported. Analytical data confirmed the identity of the two isomer oxo-nicotinic acids. UV-vis and potentiometric preliminary data showed that AI(III) does not form complexes with 1,6-dihydro-2-methyl-6-oxo-nicotinic acid ethyl ester in solution, as expected, but with 1,4-dihydro-2-methyl-4-oxo-nicotinic acid. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.053

文献信息

• [EN] ARYLMETHYLENE HETEROCYCLIC COMPOUNDS AS KV1.3 POTASSIUM SHAKER CHANNEL BLOCKERS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES D'ARYLMÉTHYLÈNE UTILISÉS EN TANT QUE BLOQUEURS DES CANAUX POTASSIQUES KV1.3 DE TYPE SHAKER
  申请人：DE SHAW RES LLC

  公开号：WO2021071806A1

  公开（公告）日：2021-04-15

  A compound of Formula (I) or a pharmaceutically acceptable salt thereof is described, wherein the substituents are as defined herein. Pharmaceutical compositions comprising the same and method of using the same are also described.

  描述了化合物的公式（I）或其药学上可接受的盐，其中取代基如本文所定义。还描述了包含相同化合物的药物组合物以及使用该药物的方法。
• Discovery and SAR of novel Naphthyridines as potent inhibitors of spleen tyrosine kinase (SYK)
  作者：Charles L Cywin、Bao-Ping Zhao、Daniel W McNeil、Matt Hrapchak、Anthony S Prokopowicz、Daniel R Goldberg、Tina M Morwick、Amy Gao、Scott Jakes、Mohammed Kashem、Ronald L Magolda、Richard M Soll、Mark R Player、Mark A Bobko、James Rinker、Renee L DesJarlais、Michael P Winters

  DOI：10.1016/s0960-894x(03)00163-x

  日期：2003.4

  The discovery of novel 5,7-disubstituted[1,6]naphthyridines as potent inhibitors of Spleen Tyrosine Kinase (SYK) is discussed. The SAR reveals the necessity for a 7-aryl group with preference towards para substitution and that this in combination with 5-aminoalkylamino substituents further improved the potency of the compounds. The initial SAR as well as a survey of the other positions is discussed

  讨论了新型的5,7-二取代的[1,6]萘啶作为脾酪氨酸激酶（SYK）的有效抑制剂的发现。SAR揭示了7-芳基优先于对位取代的必要性，并且其与5-氨基烷基氨基取代基的结合进一步提高了化合物的效力。详细讨论了初始比吸收率以及其他位置的调查。
• Heterocyclic Inhibitors of Mek and Methods of Use Thereof
  申请人：Marlow Allison L.

  公开号：US20080280957A1

  公开（公告）日：2008-11-13

  Disclosed are MEK inhibitors useful in the treatment of hyperproliferative diseases, such as cancer and inflammation, in mammals, and inflammatory conditions. Also disclosed are methods of using such compounds in the treatment of hyperproliferative diseases in mammals and pharmaceutical compositions containing such compounds.

  本发明揭示了MEK抑制剂，其在哺乳动物的高增殖性疾病，如癌症和炎症，以及炎症状况的治疗中有用。还揭示了使用这些化合物治疗哺乳动物高增殖性疾病的方法和含有这些化合物的制药组成物。
• HETEROCYCLIC INHIBITORS OF MEK AND METHODS OF USE THEREOF
  申请人：Marlow Allison L.

  公开号：US20110183981A1

  公开（公告）日：2011-07-28

  Disclosed are compounds of the Formula I and pharmaceutically acceptable salts and prodrugs thereof, wherein R 1 , R 2 , R 7 , R 8 and R 9 , W, X and Y are as defined in the specification. Such compounds are MEK inhibitors and useful in the treatment of hyperproliferative diseases, such as cancer and inflammation, in mammals, and inflammatory conditions. Also disclosed are methods of using such compounds in the treatment of hyperproliferative diseases in mammals and pharmaceutical compositions containing such compounds.

  本发明涉及公式I的化合物及其药学上可接受的盐和前药，其中R1、R2、R7、R8和R9，W、X和Y的定义如规范中所述。这些化合物是MEK抑制剂，可用于治疗哺乳动物的高增殖性疾病，如癌症和炎症以及炎症病症。本发明还涉及使用这些化合物治疗哺乳动物的高增殖性疾病的方法和包含这些化合物的制药组合物。
• DIHYDROPYRIDIN SULFONAMIDES AND DIHYDROPYRIDIN SULFAMIDES AS MEK INHIBITORS
  申请人：Vernier Jean-Michel

  公开号：US20120107307A1

  公开（公告）日：2012-05-03

  This invention concerns N-(ortho phenylamino dihydropyridyl)sulfonamides and N-(ortho phenylamino dihydropyridyl), N′-alkyl sulfamides which are inhibitors of MEK and are useful in the treatment of cancer and other hyperproliferative diseases.

  该发明涉及N-(邻苯氨基二氢吡啶基)磺酰胺和N-(邻苯氨基二氢吡啶基)、N'-烷基磺酰胺，它们是MEK抑制剂，可用于治疗癌症和其他过度增殖性疾病。