O-(3-phenyl-2-propynyl) hydroxylamine hydrochloride | 137270-28-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: O-(3-phenyl-2-propynyl) hydroxylamine hydrochloride
• 英文别名: O-(3-phenylprop-2-ynyl)hydroxylamine;hydrochloride
• CAS: 137270-28-1
• 化学式: C₉H₉NO*ClH
• 分子量: 183.637
• InChiKey: AGASWYKEXLOTGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.35
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  O-(3-phenyl-2-propynyl) hydroxylamine hydrochloride 以 甲醇 为溶剂， 反应 68.0h， 生成 (phenylpropynyl)-1,4,5,6-tetrahydropyrimidin-5-one oxime hydrochloride
  参考文献：
  名称：

  Synthesis, and In vitro and In vivo muscarinic pharmacological properties of a series of 1,6-Dihydro-5-(4 H )-pyrimidinone oximes

  摘要：

  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.

  DOI：

  10.1016/s0968-0896(98)00074-1

文献信息

• Design and Synthesis of m1-Selective Muscarinic Agonists:  (<i>R</i>)-(−)-(<i>Z</i>)-1-Azabicyclo[2.2.1]heptan-3-one, <i>O</i>-(3-(3‘-Methoxyphenyl)-2-propynyl)- oxime Maleate (CI<b>-</b>1017), a Functionally m1-Selective Muscarinic Agonist
  作者：Haile Tecle、Stephen D. Barrett、David J. Lauffer、Corinne Augelli-Szafran、Mark R. Brann、Michael J. Callahan、Bradley. W. Caprathe、Robert E. Davis、Patricia D. Doyle、David Eubanks、William Lipiniski、Tara Mirzadegan、Walter H. Moos、D. W. Moreland、Carrie B. Nelson、Michael R. Pavia、Charlotte Raby、Roy D. Schwarz、Carolyn J. Spencer、Anthony J. Thomas、Juan C. Jaen

  DOI：10.1021/jm960683m

  日期：1998.7.1

  The synthesis and SAR of a series of (Z)-(+/-)-1-azabicyclo[2.2. 1]heptan-3-one, O-(3-aryl-2-propynyl)oximes are described. The biochemistry and pharmacology of 24Z (PD 142505) and its enantiomers are highlighted. 24Z is functionally an m1-selective muscarinic agonist. Efficacy and m1 selectivity reside in the R enantiomer, (R)-24Z (CI-1017).

  一系列（Z）-（+/-）-1-氮杂双环[2.2。]的合成和SAR。1]庚烷-3-酮，O-（3-芳基-2-丙炔基）肟被描述。重点介绍了24Z（PD 142505）及其对映异构体的生物化学和药理作用。24Z在功能上是m1选择性毒蕈碱激动剂。功效和m1选择性存在于R对映异构体（R）-24Z（CI-1017）中。
• New indenoindolone compounds
  申请人：——

  公开号：US20030125369A1

  公开（公告）日：2003-07-03

  Compound of formula (I): 1 wherein R represents hydrogen, optionally substituted alkyl or alkenyl, R 1 to R 8 , which may be identical or different, each represents hydrogen, optionally substituted alkyl, hydroxy, acyloxy, optionally substituted amino, carboxy, optionally substituted alkoxy, or alkenyloxy, or one of R 1 to R 8 forms, with another of R 1 to R 8 that is adjacent, an alkylenedioxy group, X represents oxygen or NR 16 wherein R 16 represents hydrogen, alkyl, aryl or arylalkyl, R 9 represents hydrogen, aryl, heteroaryl, or optionally substituted, saturated or unsaturated alkyl, isomers thereof, and addition salts thereof with a pharmaceutically acceptable acid or base. Medicinal products containing the same which are useful as anti-cancer agents.

  化合物的分子式（I）如下： 其中R代表氢，可选择地取代的烷基或烯基，R1至R8，可以相同也可以不同，每个代表氢，可选择地取代的烷基，羟基，酰氧基，可选择地取代的氨基，羧基，可选择地取代的烷氧基，或烯基氧基，或者R1至R8中的一个与相邻的另一个R1至R8形成烷二氧基基团，X代表氧或NR16，其中R16代表氢，烷基，芳基或芳基烷基，R9代表氢，芳基，杂芳基，或可选择地取代的饱和或不饱和烷基，其异构体，以及其与药用酸或碱的可接受盐。含有该化合物的药物制剂可用作抗癌剂。
• Azabicyclo oxime and amine cholinergic agents and methods of treatment
  申请人：Warner-Lambert Company

  公开号：US05318978A1

  公开（公告）日：1994-06-07

  Pharmaceutically useful nitrogen containing cyclic oxime and amine substituted compounds of the formulas I to XVI are disclosed (See specification for definitions of the substituents). Specifically, the compounds are 1-azabicyclo [3.2.1] oximes, 1-azabicyclo [3.3.1] oximes, 1-aza-4-oxobicyclo [3.3.1] oximes, 1-aza-4-oxobicyclo [3.2.1] oximes, and the corresponding amines wherein the heterocyclic ring contains 7 or 8 carbon atoms ##STR1##

  本发明揭示了具有公式I至XVI的含氮环氧酮和胺取代化合物，具有药用价值（有关取代基的定义，请参阅说明书）。具体来说，这些化合物是1-氮杂双环[3.2.1]氧酮，1-氮杂双环[3.3.1]氧酮，1-氮杂-4-氧代双环[3.3.1]氧酮，1-氮杂-4-氧代双环[3.2.1]氧酮以及相应的胺，其中杂环含有7或8个碳原子。
• US5318978A
  申请人：——

  公开号：US5318978A

  公开（公告）日：1994-06-07
• US5464842A
  申请人：——

  公开号：US5464842A

  公开（公告）日：1995-11-07