3'-Cyclopentyloxy-4'-methoxy-biphenyl-4-carboxylic acid amide | 171808-11-0

• 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: 3'-Cyclopentyloxy-4'-methoxy-biphenyl-4-carboxylic acid amide
• 英文别名: 4-(3-Cyclopentyloxy-4-methoxyphenyl)benzamide
• CAS: 171808-11-0
• 化学式: C₁₉H₂₁NO₃
• 分子量: 311.381
• InChiKey: XKYJZVUQHVNEJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3'-cyclopentyloxy-4'-methoxy-biphenyl-4-carboxylic acid 在 氯化亚砜 、 氨 作用下， 以 二氯甲烷 为溶剂， 生成 3'-Cyclopentyloxy-4'-methoxy-biphenyl-4-carboxylic acid amide
  参考文献：
  名称：

  Biarylcarboxamide inhibitors of phosphodiesterase IV and tumor necrosis factor-α

  摘要：

  Tumor necrosis factor-alpha (TNF-alpha) has been implicated as a key mediator in the progression of rheumatoid arthritis. Inhibitors of phosphodiesterase IV (PDE IV) have been shown to inhibit the production of TNF-alpha by elevating intracellular levels of cyclic adenosine monophosphate (cAMP). Our efforts in a series of biarylcarboxamides have led to the identification of 8j (CP-353,164) as a potent inhibitor of PDE IV and TNF-alpha production. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00097-8

文献信息

• SUBSTITUTED BIPHENYL DERIVATIVES AS PHOSPHODIESTERASE INHIBITORS
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP0745063A1

  公开（公告）日：1996-12-04
• US5650444A
  申请人：——

  公开号：US5650444A

  公开（公告）日：1997-07-22
• US5691376A
  申请人：——

  公开号：US5691376A

  公开（公告）日：1997-11-25
• [EN] SUBSTITUTED BIPHENYL DERIVATIVES AS PHOSPHODIESTERASE INHIBITORS<br/>[FR] DERIVES BIPHENYLE SUBSTITUES UTILISES COMME INHIBITEURS DE LA PHOSPHODIESTERASE
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：WO1995022520A1

  公开（公告）日：1995-08-24

  (EN) A compound of structure (I), wherein, when R8 = H: R1 = alkyl, cycloalkyl, arylalkyl, aryl; R2 = cycloalkyl, aryl, C3-C10 alkyl; X, Y = O, S(O)n, NH; Z = CH2OH, NHSO2R3, CHO, CO2R3, CONHR4R5, CN, COR6, H, halo, NHCN, NHCONR4R5, CONR4OR5, CONR4NR5R6, 1-tetrazole, S(O)nOH, S(O)nNR3R4, C=NOH, C(=N(OH)NH2, OCONR7R6, P(O)(OR4)2, NH2, SH, OH, OS(O)2R3, C(O)CO2R3, C(O)CONR3R4, CH(OH)CO2R3, CHFCO2R3, CF2CO2R3, CH(OH)CONR3R4, CF2CONR3R4, C=NNH2, C(=NOC(=O)R3)R4, C(=NNHC(=O)R3)R4, C(=NOH)R3, C(=NNR3)R4, NHC(=O)R6 or C(O)CONH2; R3, R4, R5, R6, R7 = hydrogen, alkyl, aryl, aryalkyl, cycloalkyl, or fluoroalkyl; or a compound of Structure I, wherein: R1 = alkyl, cycloalkyl, aryalkyl, or aryl; R2 = cycloalkyl, aryl, or alkyl; X, Y = CH2, O, S(O)n), or NH; R3, R4, R5, R6, R7 are each, independently, hydrogen, alkyl, aryl, aryalkyl, cycloalkyl, or fluoroalkyl; R8 = CO2R3, CONR3, or R8 and Z are concatenated such that R8Z = C(O)NHNHC(O), (CH2)mC(=W), V(CH2)mC(=W), or VnCH=CH(CH2)nC(=W); where V = O, S(O)n, NH; W = O, NOH, NHNH2, NOC(O)CH3, or NNHC(O)CH3; halo = Cl, Br, or I; fluoroalkyl = CF3CHF2, CH2F, CH2CF3, C2F5; cycloalkyl = C3-C6 cycloalkyl; aryalkyl = C1-C4 aryl; aryl = phenyl, furanyl, thienyl, or pyridyl; n = 0-2; and m = 2-4 or pharmaceutically acceptable salts thereof, useful in the treatment of asthma, or allergic or inflammatory diseases, as well as methods of treatment and pharmaceutical compositions utilizing the same.(FR) L'invention concerne un composé ayant la formule (I). Dans cette fomule, lorsque R8 = H, R1 = alkyle, cycloalkyle, arylalkyle, aryle; R2 = cycloalkyle, aryle, C3-C10 alkyle; X, Y = O, S(O)n, NH; Z = CH2OH, NHSO2R3, CHO, CO2R3, CONHR4R5, CN, COR6, H, halo, NHCN, NHCONR4R5, CONR4OR5, CONR4NR5R6, 1-tétrazole, S(O)nOH, S(O)nNR3R4, C=NOH, C(=N(OH)NH2, OCONR7R6, P(O)(OR4)2, NH2, SH, OH, OS(O)2R3, C(O)CO2R3, C(O)CONR3R4, CH(OH)CO2R3, CHFCO2R3, CF2CO2R3, CH(OH)CONR3R4, CF2CONR3R4, C=NNH2, C(=NOC(=O)R3)R4, C(=NNHC(=O)R3)R4, C(=NOH)R3, C(=NNR3)R4, NHC(=O)R6 or C(O)CONH2; R3, R4, R5, R6, R7 = hydrogène, alkyle, aryle, aryalkyle, cycloalkyle, ou fluoroalkyle; ou un composé de la formule (I), où R1 = alkyle, cycloalkyle, aryalkyle, or aryle; R2 = cycloalkyle, aryle, ou alkyle; X, Y = CH2, O, S(O)n), ou NH; R3, R4, R5, R6, R7 sont chacun d'une manière indépendante un hydrogène, alkyle, aryle, aryalkyle, cycloalkyle, ou fluoroalkyle; R8 = CO2R3, CONR3, ou R8 et Z sont reliés pour que R8Z = C(O)NHNHC(O), (CH2)mC(=W), V(CH2)mC(=W); ou VnCH=CH(CH2)nC(=W); où V = O, S(O)n, NH; W = O, NOH, NHNH2, NOC(O)CH3, ou NNHC(O)CH3; halo = Cl, Br, or I; fluoroalkyle = CF3CHF2, CH2F, CH2CF3, C2F5; cycloalkyle = C3-C6 cycloalkyle; aryalkyle = C1-C4 aryle; aryle = phényle, furanyle, thiényle, or pyridyle; n = 0-2; et m = 2-4. L'invention concerne également les sels de ces composés, acceptables sur le plan pharmaceutique. Ces produits sont utiles pour le traitement de l'asthme, d'allergies ou de maladies inflammatoires. L'invention concerne également des compositions pharmaceutiques contenant ces produits et leur utilisation.
• Biarylcarboxamide inhibitors of phosphodiesterase IV and tumor necrosis factor-α
  作者：R.J. Chambers、A. Marfat、J.B. Cheng、V.L. Cohan、D.B. Damon、A.J. Duplantier、T.A. Hibbs、T.H. Jenkinson、K.L. Johnson、K.G. Kraus、E.R. Pettipher、E.D. Salter、J.T. Shirley、J.P. Umland

  DOI：10.1016/s0960-894x(97)00097-8

  日期：1997.3

  Tumor necrosis factor-alpha (TNF-alpha) has been implicated as a key mediator in the progression of rheumatoid arthritis. Inhibitors of phosphodiesterase IV (PDE IV) have been shown to inhibit the production of TNF-alpha by elevating intracellular levels of cyclic adenosine monophosphate (cAMP). Our efforts in a series of biarylcarboxamides have led to the identification of 8j (CP-353,164) as a potent inhibitor of PDE IV and TNF-alpha production. (C) 1997 Elsevier Science Ltd.