(2-carboxy-5-pyridyl)acetic acid dimethyl ester | 138834-53-4

• 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: (2-carboxy-5-pyridyl)acetic acid dimethyl ester
• 英文别名: 2-Carbomethoxy-5-pyridylacetic acid methylester；Methyl 5-(2-methoxy-2-oxoethyl)pyridine-2-carboxylate
• CAS: 138834-53-4
• 化学式: C₁₀H₁₁NO₄
• 分子量: 209.202
• InChiKey: CKIHWTOCBZNZCI-UHFFFAOYSA-N

物化性质

• 沸点：
  330.0±32.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2-carboxy-5-pyridyl)acetic acid dimethyl ester 在 氢氧化钾 、 sodium hydride 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 30.33h， 生成 3-(2,4-Diaminopteridin-6-yl)-2-(6-methoxycarbonylpyridin-3-yl)propanoic acid
  参考文献：
  名称：

  Analogues of Methotrexate in Rheumatoid Arthritis. 1. Effects of 10-Deazaaminopterin Analogues on Type II Collagen-Induced Arthritis in Mice

  摘要：

  Carbonation of the dianions (LDA) of 5-methylthiophene-2-carboxylic, 2-methylpyridine-5-carboxylic, and 3-methylpyridine-6-carboxylic acids provided the respective carboxy heteroarylacetic acids. The crude diacids were directly esterified in MeOH-HCl to afford the diesters. Alkylation of the sodio anions with ethyl iodide yielded the appropriate a-ethyl diesters. The anions of the various diester substrates were then alkylated by 2,4-diamino-6-(bromomethyl)-pteridine followed by ester saponification at room temperature to afford the respective 2,4-diamino-4-deoxy-10-carboxy-10-deazapteroic acids. The 10-carboxyl group was readily decarboxylated by heating in DMSO at temperatures of 110-135 degrees C to give the diamino 10-deaza heteropteroic acid intermediates. Coupling with diethyl L-glutamate followed by ester hydrolysis afforded the target aminopterins. The analogues were evaluated for antiinflammatory effect in the mouse type II collagen model. The thiophene analogue of 10-ethyl-10-deazaaminopterin was found to be an effective inhibitor in terms of reduced visual evidence of inflammation and swelling as determined by caliper measurement.

  DOI：

  10.1021/jm9505526
• 作为产物：
  描述：

  methyl 5-(chlorocarbonyl)pyridine-2-carboxylate 在 silver(l) oxide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 生成 (2-carboxy-5-pyridyl)acetic acid dimethyl ester
  参考文献：
  名称：

  Novel inhibitors of prolyl 4-hydroxylase

  摘要：

  A series of 5-acyl sulfonamides derived from pyridine-2,5-dicarboxylic acid (15) has been prepared and several members of this series have been shown to be more potent, in vitro, as inhibitors of prolyl 4-hydroxylase than 15. Several chain-extended pyridinedicarboxylic acids have also been prepared and shown to be potent inhibitors of prolyl 4-hydroxylase. The structure-activity in both these series is discussed. The results indicate that the 5-carboxylic acid binding site, in the enzyme, can accept a carboxylic acid or an acyl sulfonamide equally well. This indicates a much greater degree of freedom in this distal carboxylic acid binding site than is predicted by the current theorical model of the active site.

  DOI：

  10.1021/jm00083a001

文献信息

• Heteroaroyl 10-deazaamino-pterine compounds and use for rheumatoid
  申请人：SRI International

  公开号：US05354751A1

  公开（公告）日：1994-10-11

  There is disclosed certain heteroaroyl 10-deazaaminopterin and 5, 10 and 8, 10 di deazaminopterin compounds and their use for treatment of rheumatoid arthritis and related diseases and preparative process. Also disclosed are 10 alkenyl-(and alkynyl) 10-deazaminopterins also disclosed for treatment of rheumatoid arthritis and for leukemia and ascites tumors and preparative process.

  本文披露了某些异芳基10-脱氨甲葉酸和5、10以及8、10二脱氨甲葉酸化合物及其用于治疗类风湿性关节炎和相关疾病的方法和制备过程。同时还披露了用于治疗类风湿性关节炎、白血病和腹水瘤的10烯基-(和炔基)10-脱氨甲葉酸化合物及其制备过程。
• US5354751A
  申请人：——

  公开号：US5354751A

  公开（公告）日：1994-10-11
• [EN] HETEROAROYL-10-DEAZAAMINOPTERINS FOR TREATMENT OF INFLAMMATION<br/>[FR] HETEROAROYL-10-DESAZAAMINOPTERINES POUR LE TRAITEMENT DES INFLAMMATIONS
  申请人：SRI INTERNATIONAL

  公开号：WO1993022315A1

  公开（公告）日：1993-11-11

  (EN) The invention relates to certain heteroaroyl-10-deazaaminopterin compounds, as well as a method and composition employing certain heteroaroyl-10-deazaaminopterin compounds for the treatment of inflammatory disease, such as rheumatoid arthritis.(FR) L'invention concerne certaines hétéroaroyl-10-désazaaminoptérines ainsi qu'un procédé et une composition utilisant certaines hétéroaroyl-10-désazaaminoptérines pour le traitement de maladies inflammatoires telles que la polyarthrite rhumatoïde.