(RS)-4-(3-fluoro-phenylamino)-1-(acenaphthen-1-yl)-piperidine-4-carbonitrile | 254097-80-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (RS)-4-(3-fluoro-phenylamino)-1-(acenaphthen-1-yl)-piperidine-4-carbonitrile
• 英文别名: 1-(1,2-dihydroacenaphthylen-1-yl)-4-(3-fluoroanilino)piperidine-4-carbonitrile
• CAS: 254097-80-8
• 化学式: C₂₄H₂₂FN₃
• 分子量: 371.457
• InChiKey: OFNPIQSCTNZDEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 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：
  4

反应信息

• 作为反应物：
  描述：

  (RS)-4-(3-fluoro-phenylamino)-1-(acenaphthen-1-yl)-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 8-Acenaphthen-1-yl-1-(3-fluoro-phenyl)-1,3,8-triaza-spiro[4.5]decan-4-one
  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 (RS)-4-(3-fluoro-phenylamino)-1-(acenaphthen-1-yl)-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

• Diaza-spiro[3,5] nonane derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US06113527A1

  公开（公告）日：2000-09-05

  The invention relates to compounds of the general formula ##STR1## wherein R.sup.1 is C.sub.6-12 -cycloalkyl, optionally substituted by lower alkyl or C(O)O lower alkyl, indan-1-yl or indan-2-yl, optionally substituted by lower alkyl; acenaphthen-1-yl; bicyclo[3.3.1]non-9-yl, octahydro-inden-2-yl; 2,3-dihydro-1H-phenalen-1-yl; 2,3,3a,4,5,6-hexahydro-1H-phenalen-1-yl, decahydro-azulen-2-yl; bicyclo[6.2.0]dec-9-yl; decahydro-naphthalen-1-yl, decahydro-naphthalen-2-yl; tetrahydro-naphthalen-1-yl, tetrahydro-naphthalen-2-yl or 2-oxo-1,2-diphenyl-ethyl; R.sup.2 is .dbd.O or hydrogen, R.sup.3 is hydrogen, isoindolyl-1,3-dione, lower alkoxy, lower alkyl, amino, benzyloxy, --CH.sub.2 OR.sup.5 or --CH.sub.2 N(R.sup.5).sub.2 ; R.sup.4 is hydrogen or --CH.sub.2 OR.sup.5 ; R.sup.5 is hydrogen or lower alkyl; ##STR2## is cyclohexyl or phenyl, optionally substituted by lower alkyl, halogen or alkoxy; to racemic mixtures and their corresponding enantiomers and or pharmaceutically acceptable acid addition salts thereof. The compounds of the present invention are agonists of the orphamin FQ (OFQ) receptor and therefore useful in the treatment of diseases, related to this receptor.

  该发明涉及一般式##STR1##的化合物，其中R.sup.1是C.sub.6-12-环烷基，可以选择性地被较低的烷基或C(O)O较低的烷基取代，或者是indan-1-yl或indan-2-yl，可以选择性地被较低的烷基取代；acenaphthen-1-yl；bicyclo[3.3.1]non-9-yl；八氢基-茚-2-yl；2,3-二氢-1H-苯莰-1-yl；2,3,3a,4,5,6-六氢-1H-苯莰-1-yl；十氢基-茚-2-yl；bicyclo[6.2.0]庚-9-yl；十氢基-萘-1-yl；十氢基-萘-2-yl；四氢基-萘-1-yl；四氢基-萘-2-yl或2-氧代-1,2-二苯基-乙基；R.sup.2是.dbd.O或氢，R.sup.3是氢，异吲哚基-1,3-二酮，较低的烷氧基，较低的烷基，氨基，苄氧基，--CH.sub.2OR.sup.5或--CH.sub.2N(R.sup.5).sub.2；R.sup.4是氢或--CH.sub.2OR.sup.5；R.sup.5是氢或较低的烷基；##STR2##是环己基或苯基，可以选择性地被较低的烷基，卤素或烷氧基取代；对于该发明的化合物的外消旋混合物及其相应的对映体和/或药学上可接受的酸盐。本发明的化合物是orphamin FQ（OFQ）受体的激动剂，因此在与该受体相关的疾病的治疗中非常有用。
• US6113527A
  申请人：——

  公开号：US6113527A

  公开（公告）日：2000-09-05
• 8-Acenaphthen-1-yl-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one derivatives as orphanin FQ receptor agonists
  作者：Jürgen Wichmann、Geo Adam、Stephan Röver、Andrea M. Cesura、Frank M. Dautzenberg、François Jenck

  DOI：10.1016/s0960-894x(99)00385-6

  日期：1999.8

  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.