<(4-氟苯基)环己基甲基>胺 | 88536-30-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: <(4-氟苯基)环己基甲基>胺
• 英文名称: <(4-fluorophenyl)cyclohexylmethyl>amine
• 英文别名: Cyclohexyl(4-fluorophenyl)methanamine；cyclohexyl-(4-fluorophenyl)methanamine
• CAS: 88536-30-5
• 化学式: C₁₃H₁₈FN
• 分子量: 207.291
• InChiKey: OYCUPNFRMCKIHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  <(4-氟苯基)环己基甲基>胺 、 1-<4,6-bis(allylamino)-1,3,5-triazin-2-yl>-4-piperidone hydrochloride 在 盐酸 、 3 A molecular sieve 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 N,N'-Diallyl-6-(4-{[cyclohexyl-(4-fluoro-phenyl)-methyl]-amino}-piperidin-1-yl)-[1,3,5]triazine-2,4-diamine
  参考文献：
  名称：

  New triazine derivatives as potent modulators of multidrug resistance

  摘要：

  A series of 70 triazine derivatives have been synthesized and tested for their capacity to modulate multidrug resistance (MDR) in DC-3F/AD and KB-A1 tumor cells in vitro, in comparison with verapamil (VRP), a calcium channel antagonist currently used in therapy as an antihypertensive drug, which also shows MDR modulating activity. Among the 12 selected compounds, 16 (S9788) showed high MDR reversing properties in vitro (300- and 6-fold VRP at 5-mu-M in DC-3F/AD and KB-A1 cells, respectively) and induced a strong accumulation of adriamycin. The relationship between the increase of ADR accumulation and the fold reversal induced by these compounds and their lack of effects on the sensitive DC-3F cells suggest that they act mainly by inhibiting the P-glycoprotein (Pgp) catalyzed efflux of cytotoxic agents, as already described for a majority of MDR modulators. In vivo, in association with the antitumor drug vincristine (0.25 mg/kg), 16 (100 mg/kg) increased the TIC by 39% in mice bearing the resistant tumor cell line P388/VCR. According to these interesting properties, 16 was selected for a clinical development because it was more bioavailable than 34, even though it was less active.

  DOI：

  10.1021/jm00091a017
• 作为产物：
  描述：

  (4-fluorophenyl)cyclohexylhydroximinomethane 在 氨 、 氢气 作用下， 以 乙醇 为溶剂， 50.0 ℃ 、5.07 MPa 条件下， 反应 2.0h， 生成 <(4-氟苯基)环己基甲基>胺
  参考文献：
  名称：

  New triazine derivatives as potent modulators of multidrug resistance

  摘要：

  A series of 70 triazine derivatives have been synthesized and tested for their capacity to modulate multidrug resistance (MDR) in DC-3F/AD and KB-A1 tumor cells in vitro, in comparison with verapamil (VRP), a calcium channel antagonist currently used in therapy as an antihypertensive drug, which also shows MDR modulating activity. Among the 12 selected compounds, 16 (S9788) showed high MDR reversing properties in vitro (300- and 6-fold VRP at 5-mu-M in DC-3F/AD and KB-A1 cells, respectively) and induced a strong accumulation of adriamycin. The relationship between the increase of ADR accumulation and the fold reversal induced by these compounds and their lack of effects on the sensitive DC-3F cells suggest that they act mainly by inhibiting the P-glycoprotein (Pgp) catalyzed efflux of cytotoxic agents, as already described for a majority of MDR modulators. In vivo, in association with the antitumor drug vincristine (0.25 mg/kg), 16 (100 mg/kg) increased the TIC by 39% in mice bearing the resistant tumor cell line P388/VCR. According to these interesting properties, 16 was selected for a clinical development because it was more bioavailable than 34, even though it was less active.

  DOI：

  10.1021/jm00091a017

文献信息

• DIPEPTIDYL PEPTIDASE-IV INHIBITORS
  申请人：Kroth Heiko

  公开号：US20100009961A1

  公开（公告）日：2010-01-14

  The present invention relates generally to pyrrolidine and thiazolidine DPP-IV inhibitor compounds. The present invention also provides synthetic methods for preparation of such compounds, methods of inhibiting DPP-IV using such compounds and pharmaceutical formulations containing them for treatment of DPP-IV mediated diseases, in particular, Type-2 diabetes.
• Dipeptidyl Peptidase-IV Inhibitors
  申请人：KROTH Heiko

  公开号：US20110112051A1

  公开（公告）日：2011-05-12

  The present invention relates generally to pyrrolidine and thiazolidine DPP-IV inhibitor compounds. The present invention also provides synthetic methods for preparation of such compounds, methods of inhibiting DPP-IV using such compounds and pharmaceutical formulations containing them for treatment of DPP-IV mediated diseases, in particular, Type-2 diabetes.
• US7553861B2
  申请人：——

  公开号：US7553861B2

  公开（公告）日：2009-06-30
• US8076330B2
  申请人：——

  公开号：US8076330B2

  公开（公告）日：2011-12-13
• [EN] DIPEPTIDYL PEPTIDASE-IV INHIBITORS<br/>[FR] INHIBITEURS DE LA DIPEPTIDYL PEPTIDASE IV
  申请人：ALANTOS PHARMACEUTICALS INC

  公开号：WO2006116157A2

  公开（公告）日：2006-11-02

  (EN) The present invention relates generally to pyrrolidine and thiazolidine DPP-IV inhibitor compounds. The present invention also provides synthetic methods for preparation of such compounds, methods of inhibiting DPP-IV using such compounds and pharmaceutical formulations containing them for treatment of DPP-IV mediated diseases, in particular, Type-2 diabetes.(FR) La présente invention concerne de manière générale des composés de pyrrolidine et de thiazolidine inhibiteurs de la DPP IV. L'invention concerne également des procédés synthétiques de préparation de ces composés, des procédés d'inhibition de la DPP IV au moyen de ces composés et des formulations pharmaceutiques contenant lesdits composés pour traiter des maladies à médiation par la DPP IV, notamment le diabète de type 2.