1-Acenaphthen-1-yl-4-phenylamino-piperidine-4-carbonitrile | 254097-76-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-Acenaphthen-1-yl-4-phenylamino-piperidine-4-carbonitrile
• 英文别名: 4-Anilino-1-(1,2-dihydroacenaphthylen-1-yl)piperidine-4-carbonitrile
• CAS: 254097-76-2
• 化学式: C₂₄H₂₃N₃
• 分子量: 353.467
• InChiKey: AMWIBYUOHIPDPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  39.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Acenaphthen-1-yl-4-phenylamino-piperidine-4-carbonitrile 在 sodium tetrahydroborate 、 甲酸 、 乙酸酐 、 溶剂黄146 、 原甲酸三乙酯 作用下， 生成 Ro 65-6570
  参考文献：
  名称：

  8-Acenaphthen-1-yl-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one derivatives as orphanin FQ receptor agonists

  摘要：

  A series of 8-acenaphthen-1-yl-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one derivatives 1 was studied with respect to the binding affinity for the orphanin FQ (OFQ) and opioid (mu, kappa, delta) receptors. The influence of stereochemistry as well as the substitution pattern of the phenyl-ring in position 1 on the affinity for the orphanin FQ receptor and selectivity to opioid (mu, kappa, delta) receptors is discussed. The most interesting compound Ic was tested for its anxiolytic-like properties in vivo. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00385-6
• 作为产物：
  描述：

  1-羟基二氢苊 在 platinum(IV) oxide 叠氮磷酸二苯酯 、 氢气 、 potassium carbonate 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 1-Acenaphthen-1-yl-4-phenylamino-piperidine-4-carbonitrile
  参考文献：
  名称：

  8-Acenaphthen-1-yl-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one derivatives as orphanin FQ receptor agonists

  摘要：

  A series of 8-acenaphthen-1-yl-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one derivatives 1 was studied with respect to the binding affinity for the orphanin FQ (OFQ) and opioid (mu, kappa, delta) receptors. The influence of stereochemistry as well as the substitution pattern of the phenyl-ring in position 1 on the affinity for the orphanin FQ receptor and selectivity to opioid (mu, kappa, delta) receptors is discussed. The most interesting compound Ic was tested for its anxiolytic-like properties in vivo. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00385-6

文献信息

• DI-OR TRIAZA-SPIRO [4,5] DECANE DERIVATIVES
  申请人：——

  公开号：US20030176701A1

  公开（公告）日：2003-09-18

  The present invention relates to compounds of the general formula 1 wherein R 1 is C 6-10 -cycloalkyl, optionally substituted by lower alkyl or —C(O)O-lower alkyl; decahydro-naphthalen-1-yl; decahydro-naphthalen-2-yl; indan-1-yl or indan-2-yl, optionally substituted by lower alkyl; decahydro-azulen-2-yl; bicyclo[6.2.0]dec-9-yl; acenaphthen-1-yl; 2,3-dihydro-1H-phenalen-1-yl; 2,3,3a,4,5,6-hexahydro-1H-phenalen-1-yl or octahydro-inden-2-yl; R 2 is hydrogen; lower alkyl; ═O or phenyl, optionally substituted by lower alkyl, halogen or alkoxy; 2 is cyclohexyl or phenyl, optionally substituted by lower alkyl, halogen or alkoxy; X is —CH(OH)—; —C(O)—; —CHR 3 —; —CR 3 ═; —O—; —S—; —CH(COOR 4 )— or —C(COOR 4 )═; Y is —CH 2 —; —CH═; —CH(COOR 4 )—, —C(COOR 4 )═; or —C(CN)—; R 3 is hydrogen or lower alkoxy; R 4 is lower alkyl, cycloalkyl, phenyl, or benzyl and either a or b is optionally an additional bond, and to pharmaceutically acceptable acid addition salts thereof. The compounds are agonists of the orphanin FQ (QFQ) receptor and therefore useful in the treatment of diseases, related to this receptor.

  本发明涉及一般式1的化合物， 其中， R1是C6-10环烷基，可选地被较低烷基或-C（O）O-较低烷基取代； 十氢萘-1-基；十氢萘-2-基；吲哚-1-基或吲哚-2-基，可选地被较低烷基取代； 十氢-萜烯-2-基； 双环[6.2.0]癸-9-基； 萘并环[1]苯-1-基； 2,3-二氢-1H-菲-1-基； 2,3,3a,4,5,6-六氢-1H-菲-1-基或八氢-茚-2-基； R2是氢；较低烷基；═O或苯基，可选地被较低烷基，卤素或烷氧基取代； 2是环己基或苯基，可选地被较低烷基，卤素或烷氧基取代； X是—CH（OH）—；—C（O）—；—CHR3—；—CR3═；—O—；—S—；—CH（COOR4）—或—C（COOR4）═； Y是—CH2—；—CH═；—CH（COOR4）—，—C（COOR4）═；或—C（CN）—； R3是氢或较低烷氧基； R4是较低烷基，环烷基，苯基或苯甲基； a或b是可选的额外键，以及其药学上可接受的酸盐。 这些化合物是孤儿受体FQ（QFQ）激动剂，因此在与该受体相关的疾病的治疗中有用。
• Di-or triaza-spiro(4,5)decane derivatives
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0963985A2

  公开（公告）日：1999-12-15

  The present invention relates to compounds of the general formula wherein R1is C6-10-cycloalkyl, optionally substituted by lower alkyl or -C(O)O-lower alkyl; decahydro-naphthalen-1-yl; decahydro-naphthalen-2-yl; indan-1-yl or indan-2-yl, optionally substituted by lower alkyl; decahydro-azulen-2-yl; bicyclo[6.2.0]dec-9-yl; acenaphthen-1-yl; 2,3-dihydro-1H-phenalen-1-yl; 2,3,3a,4,5,6-hexahydro-1H-phenalen-1-yl or octahydro-inden-2-yl; R2is hydrogen; lower alkyl; =O or phenyl, optionally substituted by lower alkyl, halogen or alkoxy; Ⓐis cyclohexyl or phenyl, optionally substituted by lower alkyl, halogen or alkoxy; Xis -CH(OH)-; -C(O)-; -CHR3-; -CR3=; -O-; -S-; -CH(COOR4)- or - C(COOR4)=; Yis -CH2-; -CH=; -CH(COOR4)-, -C(COOR4)=; or -C(CN)-; R3is hydrogen or lower alkoxy; R4is lower alkyl, cycloalkyl, phenyl, or benzyl and either a or b is optionally an additional bond, and to pharmaceutically acceptable acid addition salts thereof. The compounds are agonists and/or antagonists of the orphanin FQ (QFQ) receptor and therefore useful in the treatment of diseases, related to this receptor.

  本发明涉及通式如下的化合物 式中 R1为C6-10-环烷基，任选被低级烷基或-C(O)O-低级烷基取代；十氢萘-1-基；十氢萘-2-基；茚-1-基或茚-2-基，任选被低级烷基取代；十氢氮杂环烯-2-基；双环[6.2.0]癸-9-基；苊-1-基；2,3-二氢-1H-苯戊烯-1-基；2,3,3a,4,5,6-六氢-1H-苯戊烯-1-基或八氢-茚-2-基； R2是氢；低级烷基；=O或苯基，可选择被低级烷基、卤素或烷氧基取代； 是环己基或苯基，可选择被低级烷基、卤素或烷氧基取代； X是-CH(OH)-；-C(O)-；-CHR3-；-CR3=；-O-；-S-；-CH(COOR4)-或-C(COOR4)=； Y是-CH2-；-CH=；-CH(COOR4)-，-C(COOR4)=；或-C(CN)-； R3 是氢或低级烷氧基； R4 是低级烷基、环烷基、苯基或苄基 和 a 或 b 是可选的附加键、 及其药学上可接受的酸加成盐。 这些化合物是孤儿素 FQ（QFQ）受体的激动剂和/或拮抗剂，因此可用于治疗与该受体有关的疾病。
• 8-substituted-1,3,8-triazaspiro[4.5]decan-4-on derivatives
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0856514B1

  公开（公告）日：2001-06-13
• Diaza-spiro[3,5] nonane derivatives
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0970957B1

  公开（公告）日：2001-08-16
• US6071925A
  申请人：——

  公开号：US6071925A

  公开（公告）日：2000-06-06