1-甲基-1,2,3,6-四氢-4-吡啶甲酰胺 | 75532-96-6

• 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: 1-甲基-1,2,3,6-四氢-4-吡啶甲酰胺
• 英文名称: 1-methyl-1,2,5,6-tetrahydropyridine-4-carboxamide
• 英文别名: 4-carbamoyl-1-methyl-1,2,5,6-tetrahydropyridine；1-methyl-3,6-dihydro-2H-pyridine-4-carboxamide
• CAS: 75532-96-6
• 化学式: C₇H₁₂N₂O
• mdl: MFCD19205587
• 分子量: 140.185
• InChiKey: OZKAFNMISLVYEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  头孢噻肟 、 1-甲基-1,2,3,6-四氢-4-吡啶甲酰胺 生成 (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(4-carbamoyl-1-methyl-3,6-dihydro-2H-pyridin-1-ium-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
  参考文献：
  名称：

  YAMAUTI, XIROSI;KOMATSU, OTAKEH;SUGIYAMI, ISAMU;NOMOTO, SEHJITIRO

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氨基甲酰-1-甲基吡啶鎓碘化物 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以0.81 g的产率得到1-甲基-1,2,3,6-四氢-4-吡啶甲酰胺
  参考文献：
  名称：

  Carbamyl analogs of potent, nicotinic agonists: pharmacology and computer-assisted molecular modeling study

  摘要：

  To investigate how the substitution of NH2 for CH3 affects the activity of three, potent, semirigid nicotinic agonists, carbamyl analogues were synthesized. The carbamyl agonists were 1-methyl-4-carbamyl-1,2,3,6-tetrahydropyridine methiodide (1), 1-methyl-4-carbamylpiperidine methiodide (2), and 1-methyl-4-carbamylpiperazine methiodide (3). Their potencies (reciprocals of the equipotent molar ratios) at the frog neuromuscular junction with reference to carbamylcholine were 0.77, 0.052, and 0.15, respectively. The acetyl analogues were more potent by factors of 65, 175, and 17, respectively. Explanations for this variable reduction in activity were sought by using computer-assisted molecular mechanics and calculations of electrostatic potential contours. Bioactive conformations of 1-3 were assigned on the basis of a well-supported pharmacophore and the ground-state conformation of the highly potent (50 times that of carbamylcholine) prototype, isoarecolone methiodide (4). Agonist 3 and its acetyl analogue superimposed closely in their ground-state, bioactive conformations, and the differences in their electrostatic potential contours were the least among the three pairs. Accordingly, their potencies differed the least. Agonists 1 and 2 both showed greater differences (with respect to their acetyl analogues) in their electrostatic potential contours and greater differences in potency. Agonist 2, in addition, could achieve the bioactive conformation only at the expense of 2.8 kcal mol-1, and, correspondingly, its activity relative to its acetyl analogue was lowest of all.

  DOI：

  10.1021/jm00122a006

文献信息

• Phenyl-Heteroaryl Derivatives and Methods of Use Thereof
  申请人：TransTech Pharma, Inc.

  公开号：US20130197007A1

  公开（公告）日：2013-08-01

  The present invention provides phenyl-heteroaryl derivatives of Formula (I) and pharmaceutically acceptable salts thereof These compounds are useful in the treatment of RAGE-mediated diseases such as Alzheimer's Disease. The present invention further relates to methods for the preparation of compounds of Formula (I) and pharmaceutically acceptable salts thereof, pharmaceutical compositions comprising such compounds, and the use of such compounds and/or pharmaceutical compositions in treating RAGE-mediated diseases.

  本发明提供了式（I）的苯基-杂环芳基衍生物及其药学上可接受的盐。这些化合物可用于治疗RAGE介导的疾病，如阿尔茨海默病。本发明还涉及制备式（I）的化合物及其药学上可接受的盐的方法，包括这种化合物的制药组合物，以及使用这种化合物和/或制药组合物治疗RAGE介导的疾病。
• Piperidine compounds and their preparation and use
  申请人：NOVO NORDISK A/S

  公开号：EP0259621A2

  公开（公告）日：1988-03-16

  New piperidine compounds having the formula wherein at least one of R³, R⁴, and R⁵ are and the other independently are H or C1-6-alkyl, wherein Rʹ is H, C1-8-alkyl, phenyl, thienyl, cyclopropyl, or C1-3-alkoxymethyl; and R¹ and R⁶ independently are H or C1-6-alkyl and a salt thereof with a pharmaceutically-acceptable acid. The new compounds are useful in improving the cognitive functions of the forebrain and hippocampus of mammals, and are useful in the treatment of Alzheimer's disease.

  具有以下式子的新哌啶化合物 式中 R³、R⁴ 和 R⁵ 中至少有一个是 和 R⁵ 中至少有一个是 H 或 C1-6-烷基、 其中 Rʹ 是 H、C1-8-烷基、苯基、噻吩基、环丙基或 C1-3- 烷氧基甲基；以及 R¹和 R⁶各自为 H 或 C1-6- 烷基 及其与药学上可接受的酸的盐。 新化合物有助于改善哺乳动物前脑和海马的认知功能，并可用于治疗阿尔茨海默氏症。
• Paglietti, Giuseppe; Sanna, Paolo; Nuvole, Antonio, Journal of Chemical Research, Miniprint, 1983, # 10, p. 2326 - 2342
  作者：Paglietti, Giuseppe、Sanna, Paolo、Nuvole, Antonio、Soccolini, Francesco、Acheson, R. Morrin

  DOI：——

  日期：——
• Moracci, Franco Micheletti; Tortorella, Silvano, Synthetic Communications, 1983, vol. 13, # 14, p. 1225 - 1234
  作者：Moracci, Franco Micheletti、Tortorella, Silvano

  DOI：——

  日期：——
• PAGLIETTI, G.;SANNA, P.;NUVOLE, A.;SOCCOLINI, F.;ACHESON, R. M., J. CHEM. RES. MICROFICHE, 1983, N 10, 245
  作者：PAGLIETTI, G.、SANNA, P.、NUVOLE, A.、SOCCOLINI, F.、ACHESON, R. M.

  DOI：——

  日期：——