1,2,5,6-tetrahydropyridine-3-carboxaldehyde hydrochloride | 114485-48-2

• 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: 1,2,5,6-tetrahydropyridine-3-carboxaldehyde hydrochloride
• 英文别名: 1,2,5,6-tetrahydro-pyridine-3-carbaldehyde ; hydrochloride；1,2,5,6-Tetrahydro-pyridin-3-carbaldehyd; Hydrochlorid；1,2,5,6-tetrahydropyridin-3-carboxaldehyde hydrochloride；1,2,3,6-tetrahydropyridine-5-carbaldehyde;hydrochloride
• CAS: 114485-48-2
• 化学式: C₆H₉NO*ClH
• 分子量: 147.605
• InChiKey: JZYYOVHUYMFCRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.53
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2,5,6-tetrahydropyridine-3-carboxaldehyde hydrochloride 在 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (E)-N-methoxy-1-(1-prop-2-ynyl-3,6-dihydro-2H-pyridin-5-yl)methanimine
  参考文献：
  名称：

  1-Alkyl-1,2,5,6-tetrahydropyridine-3-carboxaldehyde-O-alkyl-oximes: a new class of potent orally active muscarinic agonists related to arecoline

  摘要：

  On the basis of the knowledge acquired from basic studies of several known arecoline derivatives about the structural requirements for potent agonistic activity and oral efficacy, a series of 1-alkyl-1,2,5,6-tetrahydropyridine-3-carboxaldehyde-O-alkyl-oximes was synthesized and biologically evaluated in a battery of in vitro and in vivo assays. The most interesting molecules to emerge from the primary screening, 1,2,5,6-tetrahydropyridine-3-carboxaldehyde-O-methyloxime hydrochloride (11, RU 35963), 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxaldehyde-O-methyloxime hydrochloride (12, RU 35926), and 1,2,5,6-tetrahydropyridine-3-carboxaldehyde-O-propargyloxime hydrochloride (30, RU 47029) and 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxaldehyde-O-propargyloxime hydrochloride (33, RU 35986), were evaluated more extensively, and their cholinomimetic profile was compared with that of the parent molecule, arecoline. The pharmacological results after oral administration to mice and rats revealed that their efficacy is 2-3 orders of magnitude higher than that of arecoline, and, in addition, they show a longer duration of action. The 4 aldoximes showed anti-amnesic properties in many respects superior to those of arecoline. Their anti-amnesic doses were 2 orders of magnitude lower than those inducing obvious cholinergic symptoms, and 3-5 orders of magnitude lower than the lethal doses. These new compounds can be regarded as potential candidates for clinical studies in AD (Alzheimer's disease) patients.

  DOI：

  10.1016/0223-5234(91)90128-a
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 作用下， 生成 1,2,5,6-tetrahydropyridine-3-carboxaldehyde hydrochloride
  参考文献：
  名称：

  Wohl; Losanitsch, Chemische Berichte, 1907, vol. 40, p. 4695

  摘要：

  DOI：

文献信息

• Compounds of 1,2,5,6-tetrahydropyridin-3-carboxaldehyde oxime which are
  申请人：Roussel UCLAF

  公开号：US05219872A1

  公开（公告）日：1993-06-15

  Compounds useful in the treatment of Alzheimer's disease, senile dementia, or memory disorders which have the formula ##STR1## in which R represents a hydrogen atom, a linear, branched or cyclic alkyl radical, saturated or unsaturated, containing up to 8 carbon atoms, possibly substituted by a free or esterified carboxy radical or R represents an aralkyl radical containing up to 10 carbon atoms and R' represents a linear or branched, saturated or unsaturated, alkyl radical, containing up to 8 carbon atoms, a radical --COalk.sub.1 or a radical --(CH.sub.2).sub.2 N(alk.sub.2).sub.2, alk.sub.1 and alk.sub.2 representing an alkyl radical containing up to 8 carbon atoms, as well as their addition salts with acids. Also compositions containing the same, method of preparation and method of treatment using the same.

  用于治疗阿尔茨海默病、老年性痴呆症或记忆障碍的化合物，其分子式为##STR1##其中R代表氢原子、含有最多8个碳原子的直链、支链或环烷基基团，饱和或不饱和，可能被自由或酯化的羧基基团取代，或者R代表含有最多10个碳原子的芳基烷基基团，R'代表含有最多8个碳原子的直链或支链，饱和或不饱和的烷基基团，一个基团--COalk.sub.1或一个基团--(CH.sub.2).sub.2 N(alk.sub.2).sub.2，其中alk.sub.1和alk.sub.2代表含有最多8个碳原子的烷基基团，以及它们与酸形成的盐。还包括含有这些化合物的组合物，制备方法和使用这些化合物的治疗方法。
• Wohl; Herzberg; Losanitsch, Chemische Berichte, 1905, vol. 38, p. 4163
  作者：Wohl、Herzberg、Losanitsch

  DOI：——

  日期：——
• US5219872A
  申请人：——

  公开号：US5219872A

  公开（公告）日：1993-06-15
• US5391754A
  申请人：——

  公开号：US5391754A

  公开（公告）日：1995-02-21
• US5532375A
  申请人：——

  公开号：US5532375A

  公开（公告）日：1996-07-02