5-Amino-6-methyl-cinchomeronsaeure | 5442-82-0

• 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
• 英文名称: 5-Amino-6-methyl-cinchomeronsaeure
• 英文别名: 5-Amino-6-methylpyridine-3,4-dicarboxylic acid
• CAS: 5442-82-0
• 化学式: C₈H₈N₂O₄
• 分子量: 196.163
• InChiKey: DJLBIUFTBMJHPG-UHFFFAOYSA-N

物化性质

• 熔点：
  248 °C
• 沸点：
  581.4±50.0 °C(Predicted)
• 密度：
  1.553±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  5-Amino-6-methyl-cinchomeronsaeure 在 甲醇 、 lithium aluminium tetrahydride 、 乙醚 、 二氯甲烷 、 硫酸 、 水 、 sodium nitrite 作用下， 生成 2-甲基-3-羟基-4,5-二羟甲基吡啶
  参考文献：
  名称：

  Lithium Aluminum Hydride Reduction of Pyridine Carboxylic Esters: Synthesis of Vitamin B₆

  摘要：

  DOI：

  10.1021/ja01145a040
• 作为产物：
  描述：

  3-amino-5-cyano-2-methyl-isonicotinic acid methyl ester 在 盐酸 作用下， 生成 5-Amino-6-methyl-cinchomeronsaeure
  参考文献：
  名称：

  The Synthesis of 6-Chloropyridoxine. The Hydride Reduction of Pyridinedicarboxylic Acids

  摘要：

  DOI：

  10.1021/ja01556a021

文献信息

• Derivatives of 7-amino 2-dialkylaminoalkyl-1H-pyrrol[3.4-c] pyridine-1.3(2H)-dione with effect against cataract
  申请人：FARMIGEA S.P.A.

  公开号：EP0361566A1

  公开（公告）日：1990-04-04

  The invention refers to new efficacious products for the prevention and therapy of cataract, derivatives of 7-amino-2-dialkylaminoalkyl-1H-pyrrol [3.4-c] pyridine-1.3(2H)-dione of general formula, I where R represents an atom of hydrogen, a methyl or ethyl group, R′ an atom of hydrogen or of chlorine, the chain between the two atoms of nitrogen of the lateral chain consists of 2 or 3 atoms of carbon (n=2.3) and it may be linear or branched with small groups of alkyls (R˝=hydrogen, methyl or ethyl); groups R‴ and RIV are CH₃ C₂H₅, or they are part of a ring such as the one of pyrrolidine, of piperidine, of N-methylpiperazine, of β-hydroxyethylpiperazine or of morpholine.

  该发明涉及一种新的有效产品，用于预防和治疗白内障，其为一般式I的7-氨基-2-二烷基氨基烷基-1H-吡咯[3.4-c]吡啶-1,3(2H)-二酮的衍生物，其中R代表氢原子，甲基或乙基基团，R'代表氢原子或氯原子，侧链中两个氮原子之间的链由2或3个碳原子（n=2.3）组成，可以是直链或支链，带有小的烷基（R"=氢，甲基或乙基）；R‴和RIV基团为CH₃C₂H₅，或者它们是吡咯烷，哌嗪，N-甲基哌嗪，β-羟乙基哌嗪或吗啡啉环的一部分。
• Synthesis of pyrrolo[3,4-c]pyridine derivatives possessing an acid group and their in vitro and in vivo evaluation as aldose reductase inhibitors
  作者：A Da Settimo、G Primofiore、F Da Settimo、F Simorini、C La Motta、A Martinelli、E Boldrini

  DOI：10.1016/s0223-5234(96)80006-7

  日期：1996.1

  Derivatives of [pyrrolo[3,4-c]pyridin-1,3(2H)-dion-2-yl] alkanoic acids were prepared and their in vitro aldose reductase inhibitory activity was tested on rat lens enzyme. The acetic derivatives 2, 5 and 15a-d proved to be much more potent inhibitors than the propionic derivatives, 7 and 16a-d, and the iso-propionic derivatives, 3 and 6. The presence of a second planar aromatic area in the benzoyl derivatives 15a-d did not result in any increase in activity. Two of the most active compounds in vitro (2 and 5) were also evaluated in vivo as inhibitors of glutathione lens depletion in galactosemic rats. None of the compounds was found to be active in maintaining the rat lens glutathione level, suggesting possible problems of ocular bioavailability and metabolism. The aldose reductase inhibitory activity of compounds 2 and 15d was also discussed by taking into account their conformational and electronic characteristics evaluated by means of theoretical calculations.
• 2 methyl-3 acetyl-4, 5 pyridine dicarboxylic acid, lower alkyl esters thereof and intermediates
  申请人：LILLY CO ELI

  公开号：US02724714A1

  公开（公告）日：1955-11-22
• Wuest et al., Recueil des Travaux Chimiques des Pays-Bas, 1959, vol. 78, p. 226,240
  作者：Wuest et al.

  DOI：——

  日期：——
• 2-methyl-3-amino-4,5-di-hydroxymethylpyridine and its salts and the preparation thereof
  申请人：LILLY CO ELI

  公开号：US02650232A1

  公开（公告）日：1953-08-25