O-(but-2-yn-1-yl)hydroxylamine hydrochloride | 137270-08-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(but-2-yn-1-yl)hydroxylamine hydrochloride
• 英文别名: O-(2-butynyl)hydroxylamine hydrochloride；O-but-2-ynylhydroxylamine;hydrochloride
• CAS: 137270-08-7
• 化学式: C₄H₇NO*ClH
• 分子量: 121.567
• InChiKey: GVWGKAHAWPUVFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.32
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  托品酮 、 O-(but-2-yn-1-yl)hydroxylamine hydrochloride 以 甲醇 为溶剂， 反应 18.0h， 生成 N-but-2-ynoxy-8-methyl-8-azabicyclo[3.2.1]octan-3-imine
  参考文献：
  名称：

  Synthesis and Pharmacological Characterization of O-Alkynyloximes of Tropinone and N-Methylpiperidinone as Muscarinic Agonists

  摘要：

  A number of O-alkynyloximes of tropinone and N-methyl-4-piperidinone have been synthesized and evaluated for muscarinic activity. The affinities of these oximes were tested in homogenates of cerebral cortex, heart, and submandibulary glands from rats using [H-3]pirenzepine and [H-3]- N-methylscopolamine as radioligands. The oximes bind to the cortical muscarinic receptors with pK(i) values varying from 3 to 7. Higher binding affinities were observed for the O-alkynyl tropinone oximes than the corresponding piperidinone analogues. Binding to the muscarinic sites in the heart and submandibulary glands was also observed but with lower affinities. Good M-1 subtype selectivity (10-fold or greater) was observed with some oximes (26a, 28a, 32a) at the cortical sites. These oximes also attenuated scopolamine-induced impairment of the water mask task in mice. Functional assays for Ma activity on the rat aorta showed that all oximes possessed M-3 agonist action but M-2 agonist activity was not observed at the endothelium-denuded rabbit aorta. Analysis of the quantitative structure-activity relationship (QSAR) indicated that the Connolly surface area is an important determinant of activity, accounting for 70% of the variation in cortical binding affinity among the oximes.

  DOI：

  10.1021/jm9708588
• 作为产物：
  描述：

  2-(but-2-yn-1-yloxy)isoindoline-1,3-dione 在 一水合肼 、 盐酸 作用下， 以 甲醇 、 二氯甲烷 、 甲基叔丁基醚 、 水 、 乙酸乙酯 为溶剂， 以2.1 g的产率得到O-(but-2-yn-1-yl)hydroxylamine hydrochloride
  参考文献：
  名称：

  [EN] AROMATIC AMIDE DERIVATIVE AND USE THEREOF IN ANTITUMOR DRUGS
  [FR] DÉRIVÉ D'AMIDE AROMATIQUE ET SON UTILISATION DANS DES MÉDICAMENTS ANTITUMORAUX
  [ZH] 一种芳香酰胺类衍生物及其在抗肿瘤药物中的应用

  摘要：

  本发明提供一种芳香酰胺类衍生物，其立体异构体，互变异构体，溶剂化物及其药学上可接受的盐，还提供了该类化合物的制备方法以及该类化合物单独的或与其他药物联合使用在预防和/治疗细胞增殖性疾病、特别是与MEK，Raf介导的癌症有关的疾病方面的应用。

  公开号：

  WO2024002210A1

文献信息

• Novel Cercosporamide Derivative
  申请人：Furukawa Akihiro

  公开号：US20090036492A1

  公开（公告）日：2009-02-05

  The present invention relates to a novel cercosporamide derivative, a pharmacologically acceptable salt thereof or an ester thereof which has an excellent hypoglycemic effect and is useful as a therapeutic and/or prophylactic agent for diabetes. A cercosporamide derivative having the general formula (I): [wherein X represents an oxygen atom or the like, R 1 represents a hydrogen atom or a C 1 -C 6 alkyl group, R 2 represents a hydrogen atom, a C 1 -C 6 alkyl group or a C 1 -C 6 halogenated alkyl group, R 3 represents a hydrogen atom or a C 1 -C 6 alkyl group, R 4 represents a C 6 -C 10 aryl group which may be substituted with one to five group(s) independently selected from Substituent Group a, or the like, n represents 1, 2 or 3, and Substituent Group a represents a halogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 halogenated alkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 alkynyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 halogenated alkoxy group, a C 2 -C 6 alkenyloxy group, a C 2 -C 6 alkynyloxy group and the like], a pharmacologically acceptable salt thereof or an ester thereof.

  本发明涉及一种新型的环孢霉素衍生物，其具有优异的降血糖作用，可作为糖尿病治疗和/或预防制剂使用的药物学上可接受的盐或酯。 具有以下通式（I）的环孢霉素衍生物： [其中，X代表氧原子或类似物，R1代表氢原子或C1-C6烷基，R2代表氢原子、C1-C6烷基或C1-C6卤代烷基，R3代表氢原子或C1-C6烷基，R4代表C6-C10芳基，该芳基可被一个到五个独立选择的取代基a取代，n代表1、2或3，取代基a代表卤原子、C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C2-C6炔基、C1-C6烷氧基、C1-C6卤代烷氧基、C2-C6烯氧基、C2-C6炔氧基等]，其药学上可接受的盐或酯。
• NOVEL CERCOSPORAMIDE DERIVATIVE
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP1914229B1

  公开（公告）日：2010-06-16
• Synthesis, and In vitro and In vivo muscarinic pharmacological properties of a series of 1,6-Dihydro-5-(4 H )-pyrimidinone oximes
  作者：Ralf Plate、Marc J.M. Plaum、Peter Pintar、Christan G. Jans、Thijs de Boer、Fred A. Dijcks、Ge Ruigt、John S. Andrews

  DOI：10.1016/s0968-0896(98)00074-1

  日期：1998.9

  A series of 1,6-dihydro-5-(4H)-pyrimidinone oxime derivatives I was synthesized (Scheme 1, Tables 1 and 2) and tested for muscarinic activity (Table 3) in receptor binding assays using [H-3]-oxotremorine-M (Oxo-M) and [H-3]-pirenzepine pirenzepine (Pz) as ligands. Potential muscarinic agonistic or antagonistic properties of the compounds were determined using binding studies that measured their potencies to inhibit the binding of Oxo-M and Pz. Preferential inhibition of Oxo-M binding was used as an indicator for potential muscarinic agonistic properties; this potential was confirmed in functional studies on isolated organs. The series produced a wide range of active compounds with differing degrees of selectivity in M-1, M-2, and M-3 functional models. Several compounds that have mixed agonist/antagonist profiles were able to reduce cholinergic-related cognitive impairments in models of mnemonic function. Substitutions (I, e.g. R-2 or R-3 = Me) at the 1,6-dihydro-5-(4H)pyrimidine ring disrupted binding and efficacy, whereas systematic variation of the oximes substituent R1 resulted in various degrees of potency and selectivity dependent on the nature of the substitution. (C) 1998 Elsevier Science Ltd. All rights reserved.