methyl (6aR,9R,10aR)-3-tert-butyl-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxylate | 208995-24-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 麦角林及其衍生物
• 英文名称: methyl (6aR,9R,10aR)-3-tert-butyl-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxylate
• CAS: 208995-24-8
• 化学式: C₂₁H₂₈N₂O₂
• 分子量: 340.466
• InChiKey: JBXCYTQBFQPPLY-FRFSOERESA-N

物化性质

• 沸点：
  488.619±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.141±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (6aR,9R,10aR)-3-tert-butyl-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxylate 在 吡啶 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (6aR,9R,10aR)-3-tert-Butyl-7,9-dimethyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline
  参考文献：
  名称：

  Serotonergic ergoline derivatives

  摘要：

  Novel classes of 13- and 14-tertbutyl-ergoline derivatives were prepared, and characterised in vitro for their affinity for adrenergic, dopaminergic and serotonergic binding sites. This study particularly examines the importance of the presence and the position of the tert-butyl group in conferring either significant 5-HT1A or 5-HT2 affinity and selectivity respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00166-8
• 作为产物：
  描述：

  9,10-dihydrolysergic acid methyl ester 在 镍 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 methyl (6aR,9R,10aR)-3-tert-butyl-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxylate
  参考文献：
  名称：

  Serotonergic ergoline derivatives

  摘要：

  Novel classes of 13- and 14-tertbutyl-ergoline derivatives were prepared, and characterised in vitro for their affinity for adrenergic, dopaminergic and serotonergic binding sites. This study particularly examines the importance of the presence and the position of the tert-butyl group in conferring either significant 5-HT1A or 5-HT2 affinity and selectivity respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00166-8

文献信息

• SEROTONINERGIC ERGOLINE DERIVATIVES
  申请人：PHARMACIA & UPJOHN S.p.A.

  公开号：EP0628042B1

  公开（公告）日：2001-08-16
• US5430031A
  申请人：——

  公开号：US5430031A

  公开（公告）日：1995-07-04
• [EN] SEROTONINERGIC ERGOLINE DERIVATIVES<br/>[FR] DERIVES D'ERGOLINIE SEROTONINERGIQUES
  申请人：FARMITALIA CARLO ERBA S.R.L.

  公开号：WO1994014806A1

  公开（公告）日：1994-07-07

  (EN) The present invention provides compounds of formula (I) wherein A represents OH, NH2, COOR3', OCONHR4, CONHR4, NHCOR4, NHCO2R4, NHC(X)NHR4, NHC(X)NHCOR4, (a) or (b), R1 is hydrogen or C1-4 linear or branched alkyl; R2 is hydrogen, chlorine, bromine or an S-C1-4 alkyl group; R3 and R3' are, independently, C1-5 alkyl or hydrogen, n is 0,1 or 2, m is 1 or 2; R4 is hydrogen, C1-7 alkyl, C3-7 cycloalkyl, adamantidyl (tricyclo 3.3.1.1.3,7) decan-1-yl, C1-5 alkylphenyl, C2 alkenylphenyl; C2 alkynylphenyl, phenyl optionally substituted by one or more groups selected from C1-4 alkyl, C1-3 alkoxy, methylendioxy, cyano, trifluoromethyl, hydroxy, nitro and acetyl; an optionally substituted naphthyl ring or phenyl condensed with a heterocyclic ring system having 5- or 6- ring members including 1 to 4 heteroatoms selected from nitrogen, oxygen and sulphur; a heterocyclic ring having 5 or 6 ring members including 1 or 2 heteroatoms selected from nitrogen, oxygen and sulphur which is optionally substituted by a group selected from C1-4 alkyl, phenyl optionally substituted as defined above, C1-3 alkoxy and halogen; R5 is hydrogen, C1-4 alkyl or a phenyl group and X is NH, O, S; or a pharmaceutically acceptable salt thereof. A process for their preparation and the pharmaceutical compositions comprising them are also provided.(FR) Composés répondant à la formule (I), dans laquelle A représente OH, NH2, COOR3', OCONHR4, CONHR4, NHCOR4, NHCO2R4, NHC(X)NHR4, NHC(X)NHCOR4, (a) ou (b); R1 représente hydrogène ou alkyle C1-4 linéaire ou ramifié; R2 représente hydrogène, chlore, brome ou un groupe alkyle S-C1-4; R3 et R3', indépendamment l'un de l'autre, représentent alkyle C1-5 ou hydrogène; n vaut 0, 1 ou 2; m vaut 1 ou 2; R4 représente hydrogène, alkyle C1-7, cycloalkyle C3-7, adamantidyle (tricyclo 3,3,1,1,3,7) décan-1-yle), alkylphényl C1-5, alcénylphényle C2; alcynylphényle C2, phényle éventuellement substitué par un ou plusieurs groupes sélectionnés parmi alkyle C1-4, alcoxy C1-3, méthylèndioxy, cyano, trifluorométhyle, hydroxy, nitro et acétyle, un cycle naphtyle éventuellement substitué ou phényle condensé avec un système cyclique hétérocyclique penta- ou hexagonal comprenant de 1 à 4 hétéroatomes sélectionnés parmi l'azote, l'oxygène et le soufre; un cycle hétérocyclique penta- ou hexagonal comprenant 1 ou 2 hétéroatomes sélectionnés parmi l'azote, l'oxygène et le soufre, éventuellement substitué par un groupe sélectionné parmi alkyle C1-4, phényle éventuellement substitué de la manière précitée, alcoxy C1-3 et halogène; R5 représente hydrogène, alkyle C1-4 ou un groupe phényle; et X représente NH, O ou S; ou leur sel pharmaceutiquement acceptable. On a également prévu leur procédé de préparation, et des compositions pharmaceutiques les contenant.
• Serotonergic ergoline derivatives
  作者：Sergio Mantegani、Enzo Brambilla、Carla Caccia、Gabriele Damiani、Maria Gioia Fornaretto、Robert A. McArthur、Mario Varasi

  DOI：10.1016/s0960-894x(98)00166-8

  日期：1998.5

  Novel classes of 13- and 14-tertbutyl-ergoline derivatives were prepared, and characterised in vitro for their affinity for adrenergic, dopaminergic and serotonergic binding sites. This study particularly examines the importance of the presence and the position of the tert-butyl group in conferring either significant 5-HT1A or 5-HT2 affinity and selectivity respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.