2-methoxycarbonyl-1-(3-pyridinyl)-but-1-en-3-one | 39562-54-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 2-methoxycarbonyl-1-(3-pyridinyl)-but-1-en-3-one
• 英文别名: methyl 3-pyridylmethylideneacetoacetate；β-pyridylmethylideneacetoacetic acid methyl ester；methyl (2E/Z)-3-oxo-2-(pyridin-3-ylmethylidene)butanoate；methyl-3-oxo-2-(pyridin-3-ylmethylidene)butanoate；Methyl 3-oxo-2-(pyridin-3-ylmethylidene)butanoate
• CAS: 39562-54-4
• 化学式: C₁₁H₁₁NO₃
• mdl: MFCD27950308
• 分子量: 205.213
• InChiKey: GICKLQDEXFICEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  56.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methoxycarbonyl-1-(3-pyridinyl)-but-1-en-3-one 在 palladium 10% on activated carbon 氢气 作用下， 以 甲醇 、 乙醇 、 溶剂黄146 为溶剂， 80.0 ℃ 、700.01 kPa 条件下， 反应 52.0h， 生成 N,N-dimethyl-6-[3-methyl-5-oxo-4-(pyridin-3-ylmethyl)-2,5-dihydro-1H-pyrazol-1-yl]pyridine-3-sulfonamide
  参考文献：
  名称：

  DERIVATIVES OF 2-PYRIDIN-2-YL-PYRAZOL-3(2H)-ONE, PREPARATION AND THERAPEUTIC USE THEREOF AS HIF ACTIVATORS

  摘要：

  本发明涉及新型取代二氢吡唑酮衍生物，其制备以及作为转录因子HIF激活剂的治疗用途。

  公开号：

  US20110294788A1
• 作为产物：
  描述：

  3-吡啶甲醛 在 乙酸酐 作用下， 以 苯 为溶剂， 生成 2-methoxycarbonyl-1-(3-pyridinyl)-but-1-en-3-one
  参考文献：
  名称：

  烷基1,4-二氢-2,6-二甲基-4-(吡啶基)-5-[2-(4,5-二氢-4,4-二甲基恶唑啉-2-基)的合成及平滑肌钙通道拮抗剂作用] -3-吡啶羧酸盐

  摘要：

  一组外消旋烷基1,4-二氢-2,6-二甲基-4-(3-或4-吡啶基)-5-[2-(4,5-二氢-4,4-二甲基恶唑啉-2-基) ] -3 - 吡啶羧酸盐 11a - e 是通过使用 Hantzsch 反应制备的，该反应涉及 Knoevenagel 加合物 9a - e 与 1- [2- (4,5 - 二氢 - 4,4 - 二甲基恶唑啉 - 2 - 基)] - 1 -Propen-2-amines (10)。相反，4-(2-吡啶基)类似物11f是通过亚硫酰氯介导的16的5-{N-(1,1-二甲基-2-羟乙基)氨基羰基}部分环化到5-[2- (4,5-二氢-4,4-二甲基恶唑啉-2-基)]环系统(11f)。通过使用豚鼠回肠纵向平滑肌 (GPILSM) 测定法测定体外钙通道拮抗剂活性。与参考药物硝苯地平 (IC50 = 1.43 × 10-8 M) 相比，标题化合物 11 表现出较弱的钙通道拮抗剂活性

  DOI：

  10.1002/ardp.19963290807

文献信息

• Pharmaceutical compositions containing unsymmetrical esters of
  申请人：Farbenfabriken Bayer AG

  公开号：US03932645A1

  公开（公告）日：1976-01-13

  Pharmaceutical compositions containing unsymmetrical esters of 1,4-dihydropyridine 3,5-dicarboxylic acids as the active ingredient and methods of using same. The said ingredients are unsymmetrical 1,4-dihydropyridine 3,5-dicarboxylates which are substituted at position-4 of the dihydropyridine nucleus by phenyl which contains at least one nitro, cyano, azido, alkylthio, or alkylsulphonyl substituent. The compositions have a cardiovascular activity which makes them useful for effecting coronary vascular dilation and, also, they have utility in the treatment of hypertension.

  含有不对称酯化的1,4-二氢吡啶-3,5-二羧酸的药物组合物作为活性成分，并使用方法。所述成分是在二氢吡啶核的4位被苯基取代的不对称1,4-二氢吡啶-3,5-二羧酸酯，该苯基含有至少一个硝基、氰基、叠氮基、烷基硫醚或烷基磺酰基取代基。这些组合物具有心血管活性，可用于促进冠状血管扩张，并且在治疗高血压方面具有用途。
• Studies on dihydropyridines. II. Synthesis of 4,7-dihydropyrazolo(3,4-b)pyridines with vasodilating and antihypertensive activities.
  作者：IKUO ADACHI、TERUO YAMAMORI、YOSHIHARU HIRAMATSU、KATSUNORI SAKAI、HATSUO SATO、MASARU KAWAKAMI、OSAMU UNO、MOTOHIKO UEDA

  DOI：10.1248/cpb.35.3235

  日期：——

  A series of 4-aryl-4, 7-dihydropyrazolo [3, 4-b] pyridine-5-carboxylate derivatives (72-149) was prepared and the compounds were tested for Ca-blocking activity in isolated guinea pig portal vein, antihypertensive activity in spontaneously hypertensive rats, and coronary vasodilating effect in isolated guinea pig heart. A number of derivatives had potent antihypertensive and coronary vasodilating activities. The structure-activity relationships of the series indicated that a 3-cyclopentyl or 3-cyclohexyl substituent and a hydrophobic 5-ester moiety with moderate bulkiness were effective for increasing the pharmacological potencies.

  合成了一系列4-芳基-4, 7-二氢吡唑[3, 4-b]吡啶-5-羧酸酯衍生物（72-149），并对这些化合物进行了在分离的豚鼠门静脉中的钙通道阻滞活性、自发性高血压大鼠中的抗高血压活性以及在分离的豚鼠心脏中的冠状血管扩张作用的测试。多种衍生物具有强效的抗高血压和冠状血管扩张活性。该系列的结构-活性关系表明，3-环戊基或3-环己基取代基以及具有适度体积的疏水性5-酯基团对于提高药理活性是有效的。
• IKCa-channel blockers. Part 2: Discovery of cyclohexadienes
  作者：Klaus Urbahns、Siegfried Goldmann、Jochen Krüger、Ervin Horváth、Joachim Schuhmacher、Rolf Grosser、Volker Hinz、Frank Mauler

  DOI：10.1016/j.bmcl.2004.10.063

  日期：2005.1

  Novel cyclohexadienes have been identified as potent and specific IKCa-channel blockers. In this communication we describe their synthesis as well as their chemical and biological properties. A selected derivative is being enriched in rat brain and reduces the infarct volume, intracranial pressure as well as the water content in a rat subdural hematoma model of traumatic brain injury after iv administration. (C) 2004 Elsevier Ltd. All rights reserved.
• DERIVATIVES OF 2-PYRIDIN-2-YL-PYRAZOL-3(2H)-ONE, PREPARATION AND THERAPEUTIC USE THEREOF AS HIF ACTIVATORS
  申请人：ALTENBURGER Jean-Michel

  公开号：US20110294788A1

  公开（公告）日：2011-12-01

  The present invention relates to novel substituted dihydropyrazolone derivatives, to their preparation and to their therapeutic use as activators of the transcription factor HIF.

  本发明涉及新型取代二氢吡唑酮衍生物，其制备以及作为转录因子HIF激活剂的治疗用途。
• Synthesis and Smooth Muscle Calcium Channel Antagonist Effects of Alkyl 1,4-Dihydro-2,6-dimethyl-4-(pyridinyl)-5-[2-(4,5-dihydro-4,4-dimethyloxazolin-2-yl)]-3-pyridinecarboxylates
  作者：Raymond D. Anana、Edward E. Knaus

  DOI：10.1002/ardp.19963290807

  日期：——

  vitro calcium channel antagonist activity was determined by using the guinea pig ileum longitudinal smooth muscle (GPILSM) assay. Compared to the reference drug nifedipine (IC50 = 1.43 × 10−8 M), the title compounds 11 exhibited weak calcium channel antagonist activity (10−5 to 10−6 M range). A comparison of compounds 11 having a C‐4 3‐pyridinyl substituent showed that with respect to the alkyl ester

  一组外消旋烷基1,4-二氢-2,6-二甲基-4-(3-或4-吡啶基)-5-[2-(4,5-二氢-4,4-二甲基恶唑啉-2-基) ] -3 - 吡啶羧酸盐 11a - e 是通过使用 Hantzsch 反应制备的，该反应涉及 Knoevenagel 加合物 9a - e 与 1- [2- (4,5 - 二氢 - 4,4 - 二甲基恶唑啉 - 2 - 基)] - 1 -Propen-2-amines (10)。相反，4-(2-吡啶基)类似物11f是通过亚硫酰氯介导的16的5-N-(1,1-二甲基-2-羟乙基)氨基羰基}部分环化到5-[2- (4,5-二氢-4,4-二甲基恶唑啉-2-基)]环系统(11f)。通过使用豚鼠回肠纵向平滑肌 (GPILSM) 测定法测定体外钙通道拮抗剂活性。与参考药物硝苯地平 (IC50 = 1.43 × 10-8 M) 相比，标题化合物 11 表现出较弱的钙通道拮抗剂活性