1-methyl-2-phenyl-3-pyrazolidinone | 17170-36-4

• 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: 1-methyl-2-phenyl-3-pyrazolidinone
• 英文别名: 1-methyl-2-phenyl-pyrazolidin-3-one；2-Methyl-1-phenyl-pyrazolidon-(5)；methyl-2-phenyl-3 H-pyrazolin-3-on；1-methyl-2-phenylpyrazolidin-3-one
• CAS: 17170-36-4
• 化学式: C₁₀H₁₂N₂O
• 分子量: 176.218
• InChiKey: BQVQTBHBHAITPF-UHFFFAOYSA-N

物化性质

• 沸点：
  266.5±23.0 °C(Predicted)
• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methyl-2-phenyl-3-pyrazolidinone 、 1-tert-butoxycarbonyl-3-formyl-4,6-dichloroindole-2-carboxylic acid ethyl ester 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以15%的产率得到(E)-4,6-dichloro-3-(1-methyl-3-oxo-2-phenylpyrazolidin-4-ylidenemethyl)-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and pharmacological characterisation of a conformationally restrained series of indole-2-carboxylates as in vivo potent glycine antagonists

  摘要：

  After the identification of GV150526, the indole-2-carboxylate template was further explored in order to identify novel potential anti-stroke agents. In particular, the SAR of the side chain present at the C-3 position of the indole nucleus was widely studied. In this paper, the synthesis and the pharmacological profile of a further class of conformationally restricted analogues of GV150526 as in vitro and in vivo potent glycine antagonists is reported. In particular, a pyrazolidinone derivative was identified as a potent neuroprotective agent in animal models of cerebral ischaemia. (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01141-7
• 作为产物：
  描述：

  3-oxo-2-phenylpyrazolidine-1-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 1-methyl-2-phenyl-3-pyrazolidinone
  参考文献：
  名称：

  Synthesis and pharmacological characterisation of a conformationally restrained series of indole-2-carboxylates as in vivo potent glycine antagonists

  摘要：

  After the identification of GV150526, the indole-2-carboxylate template was further explored in order to identify novel potential anti-stroke agents. In particular, the SAR of the side chain present at the C-3 position of the indole nucleus was widely studied. In this paper, the synthesis and the pharmacological profile of a further class of conformationally restricted analogues of GV150526 as in vitro and in vivo potent glycine antagonists is reported. In particular, a pyrazolidinone derivative was identified as a potent neuroprotective agent in animal models of cerebral ischaemia. (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01141-7

文献信息

• INDOLE DERIVATIVES AS NMDA ANTAGONISTS
  申请人：GLAXO WELLCOME S.p.A.

  公开号：EP0723541A1

  公开（公告）日：1996-07-31
• US5760059A
  申请人：——

  公开号：US5760059A

  公开（公告）日：1998-06-02
• US5962496A
  申请人：——

  公开号：US5962496A

  公开（公告）日：1999-10-05
• US6100289A
  申请人：——

  公开号：US6100289A

  公开（公告）日：2000-08-08
• [EN] INDOLE DERIVATIVES AS NMDA ANTAGONISTS<br/>[FR] DERIVES D'INDOLE UTILISES EN TANT QU'ANTAGONISTES DE N-METHYL-D-ASPARTATE (NMDA)
  申请人：GLAXO WELLCOME S.P.A.

  公开号：WO1995010517A1

  公开（公告）日：1995-04-20

  (EN) This invention relates to compounds of formula (I) or a salt, or metabolically labile ester thereof wherein R represents a group selected from halogen, alkyl, alkoxy, amino, alkylamino, dialkylamino, hydroxy, trifluoromethyl, trifluoromethoxy, nitro, cyano, SO2R2 or COR2 wherein R2 represents hydroxy, methoxy, amino, alkylamino, or dialkylamino; m is zero or an integer 1 or 2; R1 represents a cycloalkyl, bridged cycloalkyl, heteroaryl, bridged heterocyclic or optionally substituted phenyl or fused bicyclic carbocyclic group; A represents a C1-4 alkylene chain or the chain (CH2)pY(CH2)q wherein Y is O, S(O)n or NR3 and which chains may be substituted by one or two groups selected from C1-6 alkyl optionally substituted by hydroxy, amino, alkylamino or dialkylamino, or which chains may be substituted by the group = O; R3 represents hydrogen, alkyl or a nitrogen protecting group; n is zero or an integer from 1 to 2; p is zero or an integer from 1 to 3; q is zero or an integer from 1 to 3 with the proviso that the sum of p + q is 1, 2 or 3, which are antagonists of excitatory amino acids, to processes for the preparation and to other use in medicine.(FR) Cette invention concerne des composés de formule (I) ou bien un sel ou un ester métaboliquement labile de ces derniers. Dans cette formule, R représente un groupe choisi parmi halogène, alkyle, alcoxy, amino, alkylamino, dialkylamino, hydroxy, trifluorométhyle, trifluorométhoxy, nitro, cyano, SO2R2 ou COR2 dans lesquels R2 représente hydroxy, méthoxy, amino, alkylamino ou dialkylamino; m représente 0 ou un entier choisi entre 1 et 2; R1 représente un groupe cycloalkyle, cycloalkyle ponté, hétéroaryle, hétérocyclique ponté, ou un groupe phényle facultativement substitué ou bien un groupe carbocyclique bicyclique condensé; A représente une chaîne alkylèneC1-4 ou la chaîne (CH2)pY(CH2)q dans laquelle Y représente O, S(O)n ou NR3, ces chaînes pouvant être substituées par un ou plusieurs groupes choisis parmi alkyle C1-6 éventuellement substitué par hydroxy, amino, alkylamino ou dialkylamino, ou pouvant être substituées par le groupe = O; R3 représente hydrogène, alkyle ou un groupe protecteur azote; n vaut zéro ou représente un entier de 1 à 2; p vaut zéro ou représente un entier de 1 à 3; q vaut zéro ou représente un entier de 1 à 3, à condition que la somme de p + q soit 1, 2 ou 3. Ces composés sont des antagonistes des acides aminés excitateurs. L'invention concerne également des procédés de préparation et d'utilisation desdits composés en médecine.