1,4-dihydro-1-phenyl-indeno[1,2-c]pyrazole-3-carbonyl chloride | 127477-34-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,4-dihydro-1-phenyl-indeno[1,2-c]pyrazole-3-carbonyl chloride
• 英文别名: 1,4-Dihydro-1-phenyl-indeno [1,2-c]pyrazole-3-carbonyl chloride；1-phenyl-4H-indeno[1,2-c]pyrazole-3-carbonyl chloride
• CAS: 127477-34-3
• 化学式: C₁₇H₁₁ClN₂O
• 分子量: 294.74
• InChiKey: NOAGUXDUKWTMFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  二乙胺 、 1,4-dihydro-1-phenyl-indeno[1,2-c]pyrazole-3-carbonyl chloride 以 四氢呋喃 为溶剂， 以0.130 g的产率得到N,N-diethyl-1-phenyl-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxamide
  参考文献：
  名称：

  Synthesis, central and peripheral benzodiazepine receptor affinity of pyrazole and pyrazole-containing polycyclic derivatives

  摘要：

  A series of new pyrazole-condensed 6,5,5 tricyclic compounds were synthesized and tested to evaluate their binding affinities at both central (CBR) and peripheral (PBR) benzodiazepine receptors. Some 1-aryl-5-phenylpyrazole derivatives were also prepared and tested for comparison with their corresponding rigid tricyclic analogs. Among the newly synthesized 1-aryl-1,4-dihydro-indeno[1,2-c]pyrazoles bearing both an ethoxycarbonyl group at position 3 and a carbonyl function at the position 4, compound 4b emerged as a new potent (IC(50) = 26.4 nM) and selective CBR ligand. The 4-oxo-1-aryl-1,4-dihydro-indeno[1,2-c]pyrazole diethylamide derivative 14a was instead identified as a relatively potent (IC(50) = 124 nM) but highly selective PBR ligand.

  DOI：

  10.1016/j.farmac.2004.05.008
• 作为产物：
  描述：

  1-phenyl-1,4-dihydro-1H-indeno[1,2-c]pyrazole-3-carboxylic acid 在 氯化亚砜 作用下， 生成 1,4-dihydro-1-phenyl-indeno[1,2-c]pyrazole-3-carbonyl chloride
  参考文献：
  名称：

  Synthesis, central and peripheral benzodiazepine receptor affinity of pyrazole and pyrazole-containing polycyclic derivatives

  摘要：

  A series of new pyrazole-condensed 6,5,5 tricyclic compounds were synthesized and tested to evaluate their binding affinities at both central (CBR) and peripheral (PBR) benzodiazepine receptors. Some 1-aryl-5-phenylpyrazole derivatives were also prepared and tested for comparison with their corresponding rigid tricyclic analogs. Among the newly synthesized 1-aryl-1,4-dihydro-indeno[1,2-c]pyrazoles bearing both an ethoxycarbonyl group at position 3 and a carbonyl function at the position 4, compound 4b emerged as a new potent (IC(50) = 26.4 nM) and selective CBR ligand. The 4-oxo-1-aryl-1,4-dihydro-indeno[1,2-c]pyrazole diethylamide derivative 14a was instead identified as a relatively potent (IC(50) = 124 nM) but highly selective PBR ligand.

  DOI：

  10.1016/j.farmac.2004.05.008

文献信息

• Condensed pyrazole 3-oxo-propanenitrile derivatives
  申请人：Farmitalia Carlo Erba S.r.l.

  公开号：US05424308A1

  公开（公告）日：1995-06-13

  Condensed pyrazole 3-oxo-propanenitrile derivatives of formula (I) ##STR1## wherein X represents a --CH(R.sub.4)-- group, an oxygen atom or a --S(O).sub.n -- group where n is 0, 1 or 2; R.sub.1 represents C.sub.1 -C.sub.6 alkyl, pyridyl or unsubstituted or substituted phenyl; R.sub.2, R.sub.3 and R.sub.4 are as defined herein; and Q represents hydrogen, carboxy, C.sub.2 -C.sub.7 alkoxycarbonyl or a --CON(R.sub.a)R.sub.b group, R.sub.a and R.sub.b being as defined herein; and their pharmaceutically acceptable salts have immunomodulating activity and can be used in particular as immunomodulating agents, e.g. in the treatment of acute and chronic infections of both bacterial and viral origin, alone or in association with antibiotic agents, and in the treatment of neoplastic diseases, alone or in association with antitumoral agents, in mammals.

  化合物的式(I)为缩合吡唑3-氧代-丙腈衍生物，其中X代表--CH(R.sub.4)--基团、氧原子或--S(O).sub.n--基团，其中n为0、1或2；R.sub.1代表C.sub.1-C.sub.6烷基、吡啶基或未取代或取代的苯基；R.sub.2、R.sub.3和R.sub.4如本文所定义；Q代表氢、羧基、C.sub.2-C.sub.7烷氧基羰基或--CON(R.sub.a)R.sub.b基团，其中R.sub.a和R.sub.b如本文所定义；它们的药学上可接受的盐具有免疫调节活性，可以特别用作免疫调节剂，例如在治疗细菌和病毒的急性和慢性感染方面，单独或与抗生素剂联合使用，以及在治疗肿瘤疾病方面，单独或与抗肿瘤剂联合使用，适用于哺乳动物。
• Condensed Pyrazole 3-oxo-propanenitrile derivatives and process for their preparation
  申请人：FARMITALIA CARLO ERBA S.r.l.

  公开号：EP0347773A1

  公开（公告）日：1989-12-27

  Condensed pyrazole 3-oxo-propanenitrile derivatives of formula (I) wherein X represents a - CH(R4.)-group, an oxygen atom or a - S(O)n group where n is 0, 1 or 2; R1 represents C1-C6 alkyl, pyridyl or unsubstituted or substituted phenyl; R2, R3 and R4. are as defined herein; and Q represents hydrogen, carboxy, C2-C7 alkoxycarbonyl or a - CON(Ra)Rb group, Ra and Rb being as defined herein; and their pharmaceutically acceptable salts have immunomodulating activity and can be used in particular as immunostimulating agents, e.g. in the treatment of acute and chronic infections of both bacterial and viral origin, alone or in association with antibiotic agents, and in the treatment of neoplastic diseases, alone or in association with antitumoral agents, in mammals.

  式(I)的缩合吡唑-3-氧代丙腈衍生物 其中 X 代表-CH(R4.)-基团、氧原子或-S(O)n 基团（其中 n 为 0、1 或 2）；R1 代表 C1-C6 烷基、吡啶基或未取代或取代苯基；R2、R3 和 R4.如本文所定义；Q 代表氢、羧基、C2-C7 烷氧基羰基或-CON(Ra)Rb 基团，Ra 和 Rb 如本文所定义。例如，单独或与抗生素制剂联合用于治疗哺乳动物的细菌和病毒急性和慢性感染，单独或与抗肿瘤制剂联合用于治疗肿瘤性疾病。
• CONDENSED PYRAZOLE 3-OXO-PROPANENITRILE DERIVATIVES AND PROCESS FOR THEIR PREPARATION
  申请人：FARMITALIA CARLO ERBA S.r.l.

  公开号：EP0422051A1

  公开（公告）日：1991-04-17
• US5424308A
  申请人：——

  公开号：US5424308A

  公开（公告）日：1995-06-13
• [EN] CONDENSED PYRAZOLE 3-OXO-PROPANENITRILE DERIVATIVES AND PROCESS FOR THEIR PREPARATION
  申请人：FARMITALIA CARLO ERBA S.R.L.

  公开号：WO1989012630A1

  公开（公告）日：1989-12-28

  (EN) Condensed pyrazole 3-oxo-propanenitrile derivatives of formula (I), wherein X represents a -CH(R4)- group, an oxygen atom or a -S(O)n- group where n is 0, 1 or 2; R1 represents C1-C6 alkyl, pyridyl or unsubstituted or substituted phenyl; R2, R3 and R4 are as defined herein; and Q represents hydrogen, carboxy, C2-C7 alkoxycarbonyl or a -CON(Ra)Rb group, Ra and Rb being as defined herein; and their pharmaceutically acceptable salts have immunomodulating activity and can be used in particular as immunostimulating agents, e.g. in the treatment of acute and chronic infections of both bacterial and viral origin, alone or in association with antibiotic agents, and in the treatment of neoplastic diseases, alone or in association with antitumoral agents, in mammals.(FR) Les dérivés de 3-oxo-propane-nitrile de pyrazole condensés décrits qui sont représentés par la formule (I) où X représente un groupe -CH(R4), un atome d'oxygène ou un groupe -S(O)n- où n est égal à 0, à 1 ou à 2; R1 représente un pyridyle, un phényle substitué ou non substitué ou un alkyle de C1-C6; R2, R3 et R4 sont définis dans le descriptif; et Q représente l'hydrogène, un carboxy, un alkoxycarbonyle de C2-C7 ou un groupe -CON(Ra)Rb où Ra et Rb sont définis dans le descriptif; et leur sels pharmaceutiquement acceptables ont une activité immunomodulatrice et peuvent être utilisés notamment comme agents immunostimulateurs, par exemple dans le traitement d'infections aiguës et chroniques d'origine à la fois bactérienne et virale, seuls ou en association avec des agents antibiotiques, ainsi que dans le traitement de maladies néoplastiques, seuls ou en association avec des agents antitumoraux, chez les mammifères.