1-(5-methyl-2,3-dihydro-1H-indol-7-yl)-1-phenylmethanone | 179024-62-5

• 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-(5-methyl-2,3-dihydro-1H-indol-7-yl)-1-phenylmethanone
• 英文别名: (5-methyl-2,3-dihydro-1H-indol-7-yl)-phenylmethanone
• CAS: 179024-62-5
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: RVDBMPOJMWGUOH-UHFFFAOYSA-N

物化性质

• 熔点：
  83-84 °C
• 沸点：
  450.9±45.0 °C(Predicted)
• 密度：
  1.135±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(5-methyl-2,3-dihydro-1H-indol-7-yl)-1-phenylmethanone 生成 9-methyl-1-phenyl-6,7-dihydro-3H-[1,4]diazepino[6,7,1-hi]indol-4-one
  参考文献：
  名称：

  J. Med. Chem. 2000, 43, 4850-4867

  摘要：

  DOI：
• 作为产物：
  描述：

  5-甲基二氢吲哚 、 苯甲腈 在 三氯化铝 、 三氯化硼 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 1-(5-methyl-2,3-dihydro-1H-indol-7-yl)-1-phenylmethanone
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 4-oxo-1-phenyl-3,4,6,7-tetrahydro-[1,4]diazepino[6,7,1- hi ]indoles: novel PDE4 inhibitors

  摘要：

  A novel series of benzodiazepine derivatives have been discovered as inhibitors of PDE4 enzymes. We have found that our compounds are selective versus other PDE enzymes, and that the activity can be modulated by specific structural modifications. One compound exhibited a strong eosinophilic infiltration inhibiting action on sensitized Brown-Norway rats (compound 9, 5.1 mg/kg p.o.), moreover this compound is not emetic at 3 mg/kg i.v. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00573-9

文献信息

• Synthesis, Structure−Activity Relationships, and Pharmacological Profile of 9-Amino-4-oxo-1-phenyl-3,4,6,7-tetrahydro[1,4]diazepino[6,7,1-<i>h</i><i>i</i>]indoles:  Discovery of Potent, Selective Phosphodiesterase Type 4 Inhibitors
  作者：Catherine Burnouf、Eric Auclair、Nadine Avenel、Bernadette Bertin、Christèle Bigot、Alain Calvet、Kam Chan、Corinne Durand、Veronique Fasquelle、Frédéric Féru、Richard Gilbertsen、Henry Jacobelli、Adel Kebsi、Emmanuelle Lallier、Jacquie Maignel、Brigitte Martin、Stéphane Milano、Malika Ouagued、Yves Pascal、Marie-Pierre Pruniaux、Jocelyne Puaud、Marie-Noëlle Rocher、Christophe Terrasse、Roger Wrigglesworth、Annette M. Doherty

  DOI：10.1021/jm000315p

  日期：2000.12.1

  The synthesis, structure-activity relationships, and biological properties of a novel series of; potent and selective phosphodiesterase type 4 (PDE4) inhibitors are described. These new aminodiazepinoindoles displayed in vitro PDE4 activity with submicromolar IC50 values and PDE4 selectivity vs PDE1, -3, and -5. Specifically, one compound (CI-1044, 10e) provided efficient in vitro inhibition of TNF alpha release from hPBMC and; hWB with IC50:values of 0.34 and 0.84 muM, respectively. This compound was found to exhibit potent in vivo activity in antigen-induced eosinophil recruitment in Brown-Norway rats (ED50 = 3.2 mg/kg po) and in production of TNF alpha in Wistar fats (ED50 = 2.8; mg/kg po). No emetic side effects at therapeutic doses were observed in ferrets.
• DIAZEPINO-INDOLES INHIBITEURS DE PHOSPHODIESTERASES IV
  申请人：INSTITUT DE RECHERCHE JOUVEINAL (I.R.J)

  公开号：EP0785789A1

  公开（公告）日：1997-07-30
• US5852190A
  申请人：——

  公开号：US5852190A

  公开（公告）日：1998-12-22
• [EN] DIAZEPINO-INDOLES AS PHOSPHODIESTERASE IV INHIBITORS<br/>[FR] DIAZEPINO-INDOLES INHIBITEURS DE PHOSPHODIESTERASES IV
  申请人：INSTITUT DE RECHERCHE JOUVEINAL

  公开号：WO1996011690A1

  公开（公告）日：1996-04-25

  (EN) The use of diazepino-indole derivatives of formula (I), wherein R is hydrogen, lower alkyl or lower alkoxy, and A is mono- to trisubstituted aryl or heteroaryl, and racemic forms, enantiomers and pharmaceutically acceptable salts thereof, containing novel products, for preparing drugs useful for treating disorders requiring therapy using phosphodiesterase IV inhibitors.(FR) Application de dérivés de diazépino-indoles de formule (I), dans laquelle: R est hydrogène, alkyle inférieur, alcoxy inférieur; A est aryle ou hétéroaryle mono- à tribsubstitué, leurs formes racémiques, leur énantiomères, et leurs sels pharmaceutiquement acceptables, qui comprennent de nouveaux produits, pour la préparation de médicaments destinés au traitement des affections relevant d'une thérapie par les inhibiteurs de phosphodiestérases IV.
• Synthesis and structure–activity relationships of 4-oxo-1-phenyl-3,4,6,7-tetrahydro-[1,4]diazepino[6,7,1- hi ]indoles: novel PDE4 inhibitors
  作者：Yves Pascal、Charles R Andrianjara、Eric Auclair、Nadine Avenel、Bernadette Bertin、Alain Calvet、Frédéric Féru、Sophie Lardon、Indres Moodley、Malika Ouagued、Adrian Payne、Marie-Pierre Pruniaux、Corinne Szilagyi

  DOI：10.1016/s0960-894x(99)00573-9

  日期：2000.1

  A novel series of benzodiazepine derivatives have been discovered as inhibitors of PDE4 enzymes. We have found that our compounds are selective versus other PDE enzymes, and that the activity can be modulated by specific structural modifications. One compound exhibited a strong eosinophilic infiltration inhibiting action on sensitized Brown-Norway rats (compound 9, 5.1 mg/kg p.o.), moreover this compound is not emetic at 3 mg/kg i.v. (C) 1999 Elsevier Science Ltd. All rights reserved.