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(R)-5-Methoxy-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole | 143321-57-7

中文名称
——
中文别名
——
英文名称
(R)-5-Methoxy-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole
英文别名
(+)-CP-108,509;(R)-3-<(N-methylpyrrolidin-2-yl)methyl>-5-methoxy-1H-indole;(R)-5-methoxy-3 - (N-methylpyrrolidin-2-ylmethyl)-1H-indole;(R)-3-[(N-methylpyrrolidin-2-yl)methyl]-5-methoxy-1H-indole;5-Meo-mpmi;5-methoxy-3-[[(2R)-1-methylpyrrolidin-2-yl]methyl]-1H-indole
(R)-5-Methoxy-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole化学式
CAS
143321-57-7
化学式
C15H20N2O
mdl
——
分子量
244.337
InChiKey
MKEGUJPBCIXABO-GFCCVEGCSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    401.3±25.0 °C(Predicted)
  • 密度:
    1.139±0.06 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    2.9
  • 重原子数:
    18
  • 可旋转键数:
    3
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.47
  • 拓扑面积:
    28.3
  • 氢给体数:
    1
  • 氢受体数:
    2

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为产物:
    描述:
    3-Bromo-1-(tert-butyldimethylsilyl)-5-methoxyindole 在 lithium aluminium tetrahydride 、 正丁基锂 作用下, 以 四氢呋喃正己烷 为溶剂, 反应 27.5h, 生成 (R)-5-Methoxy-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole
    参考文献:
    名称:
    Further Studies on Oxygenated Tryptamines with LSD-like Activity Incorporating a Chiral Pyrrolidine Moiety into the Side Chain
    摘要:
    The enantiomers of 3-(N-methylpyrrolidin-2-ylmethyl)-5-methoxyindole, 1, and 3-(N-methylpyrrolidin-2-ylmethyl)-4-hydoxyindole, 3, were prepared using an asymmetric synthesis that employed (+)- or (-)-proline. A new approach was developed that had certain advantages over the synthesis originally reported for the isomers of 1. (+)-3-(N-Methylpyrrolidin-3-yl)-4-hydroxyindole, 5, was also prepared as a rigid analogue of psilocin and compared with its 5-methoxy counterpart 4. Radioligand competition assays were used to assess the affinity of compounds for the 5-HT2A receptor labeled with the agonist ligand [I-125]DOI and the antagonist ligand [H-3]MDL100907. Two-lever drug discrimination assays in rats trained to discriminate either LSD or DOI from saline were employed to assess the hallucinogen-like behavioral properties of these rigid tryptamine analogues. The receptor binding assay results clearly demonstrated a stereochemical preference for the R enantiomers that did not discriminate the position of the oxygen function. The receptor is 10-20-fold more selective for the R isomers. The affinities of the R enantiomers were virtually identical for both 1 and 3 at the agonist-labeled receptor, while racemic 4 and 5 had about one-tenth the affinity. The drug discrimination data in both LSD- and DOI-trained rats paralleled the binding data using [I-125]DOI displacement. Both (R)-1 and (R)-3 are about equipotent, comparable to DOI in activity but about 10-fold less potent than LSD. Compound 4 produced only partial substitution, even at a dose nearly 5-fold higher than for (R)-1. Based on conformational energies, it seems doubtful that these compounds bind to the 5-HT2A receptor in an ergoline-like conformation. The results also suggest that both 1 and 3 would possess LSD-like psychopharmacology in humans.
    DOI:
    10.1021/jm990325u
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文献信息

  • [EN] INDOLE DERIVATIVES
    申请人:PFIZER INC.
    公开号:WO1992006973A1
    公开(公告)日:1992-04-30
    (EN) Compounds of formula (I), wherein n is 0, 1 or 2; R1 is hydrogen; R2 is selected from hydrogen, halogen, cyano, OR4, -(CH2)m-(C=O)NR5R6, -(CH2)m-SO2NR5R6, -(CH2)m-NR7(C=O)R8, -(CH2)m-NR7SO2R8, -(CH2)m-S(O)xR8, -(CH2)m-NR7(C=O)NR5R6, -(CH2)m-NR7(C=O)OR9, and -CH=CH(CH2)yR10; R3 is selected from hydrogen and C1 to C6 linear or branched alkyl; R4 is selected from hydrogen, C1 to C6 alkyl, and aryl; R5 and R6 are independently selected from hydrogen, C1 to C6 alkyl, aryl, and C1 to C3 alkyl-aryl or R5 and R6 taken together to form a 4, 5, or 6 membered ring; R7 and R8 are independently selected from hydrogen, C1 to C6 alkyl, aryl, and C1 to C3 alkyl-aryl; R9 is selected from hydrogen, C1 to C6 alkyl, aryl, and C1 to C3 alkyl-aryl R10 is selected from -(C=O)NR5R6 and -SO2NR5R6, wherein R5 and R6 are defined as above, and -NR7(C=O)R8, -NR7SO2R8, -NR7(C=O)NR5R6, -S(O)xR8 and -NR7(C=O)OR9, wherein R7, R8, and R9 are as defined above; y is 0, 1, or 2; x is 1 or 2; m is 0, 1, 2, or 3; and the above aryl groups and the aryl moieties of the above alkylaryl groups are independently selected from phenyl and substituted phenyl, wherein said substituted phenyl may be substituted with one to three groups selected from C1 to C4 alkyl, halogen, hydroxy, cyano, carboxamido, nitro, and C1 to C4 alkoxy and the pharmaceutically acceptable salts thereof are new. These compounds are useful psychotherapeutics and are potent serotonin (5-HT1) agonists and may be used in the treatment of depression, anxiety, eating disorders, obesity, drug abuse, cluster headache, migraine, pain, chronic paroxysmal hemicrania and headache associated with vascular disorders, and other disorders arising from deficient serotonergic neurotransmission. The compounds can also be used as centrally acting antihypertensives and vasodilators.(FR) L'invention concerne des composés représentés par la formule (I), dans laquelle n est égal à 0, 1 ou 2; R1 représente hydrogène; R2 est sélectionné parmi hydrogène, halogène, cyano, OR4, -(CH2)m-(C=O)NR5R6, -(CH2)m-SO2NR5R6, -(CH2)m-NR7(C=O)R8, -(CH2)m-NR7SO2R8, -(CH2)m-S(O)xR8, -(CH2)m-NR7(C=O)NR5R6, -(CH2)m-NR7(C=O)OR9, et -CH=CH(CH2)yR10; R3 est sélectionné parmi hydrogène et alkyle C1 à C6 linéaire ou ramifié; R4 est sélectionné parmi hydrogène, alkyle C1 à C6, et aryle; R5 and R6 sont indépendamment sélectionnés parmi hydrogène, alkyle C1 à C6, aryle, et alkyle-aryle C1 à C3 ou R5 et R6 forment ensemble un composé carré, pentagonal ou hexagonal; R7 et R8 sont indépendamment sélectionnés parmi hydrogène, alkyle C1 à C6, aryle, et alkyle-aryle C1 à C3; R9 est sélectionné parmi hydrogène, alkyle C1 à C6, aryle, et alkyle-aryle C1 à C3; R10 est sélectionné parmi -(C=O)NR5R6 et -SO2NR5R6, où R5 et R6 sont définis comme précédemment; Y est égal à 0, 1 ou 2; x est égal à 1 ou 2; m est égal à 0, 1, 2 ou 3; et les groupes aryle et les fractions d'aryle précitées des groupes alkylaryle précités sont indépendamment sélectionnés parmi alkyle C1 à C4, halogène, hydroxy, cyano, carboxamido, nitro et alcoxy C1 à C4, et leurs sels pharmaceutiquement acceptables sont nouveaux. Ces composés sont d'utiles agents psychothérapeutiques et ce sont également de puissants agonistes de la sérotonine (5-HT1), en outre, ils peuvent être utilisés dans le traitement de la dépression, de l'anxiété, des dérèglements alimentaires, de l'obésité, de l'abus des médicaments, de la céphalée vasculaire de Horton, de la migraine, de la douleur, des maux de tête et des hémicrânies paroxystiques chroniques associés à des troubles vasculaires, et d'autres affections liées à une déficience de neurotransmission sérotonergique. Ces composés peuvent également être utilisés comme anti-hypertenseurs et vasodilatateurs agissant au niveau central.
    化合物的化学式为(I),其中n为0、1或2;R1为氢;R2选自氢、卤素、氰基、OR4、-(CH2)m-(C=O)NR5R6、-(CH2)m-SO2NR5R6、-(CH2)m-NR7(C=O)R8、-(CH2)m-NR7SO2R8、-(CH2)m-S(O)xR8、-(CH2)m-NR7(C=O)NR5R6、-(CH2)m-NR7(C=O)OR9和-CH=CH(CH2)yR10;R3选自氢和C1到C6的线性或支链烷基;R4选自氢、C1到C6的烷基和芳基;R5和R6独立地选自氢、C1到C6的烷基、芳基和C1到C3的烷基-芳基,或R5和R6结合形成4、5或6元环;R7和R8独立地选自氢、C1到C6的烷基、芳基和C1到C3的烷基-芳基;R9选自氢、C1到C6的烷基、芳基和C1到C3的烷基-芳基;R10选自-(C=O)NR5R6和-SO2NR5R6,其中R5和R6如上定义,以及-NR7(C=O)R8、-NR7SO2R8、-NR7(C=O)NR5R6、-S(O)xR8和-NR7(C=O)OR9,其中R7、R8和R9如上定义;y为0、1或2;x为1或2;m为0、1、2或3;上述芳基和上述烷基芳基的芳基基团独立地选自苯基和取代苯基,所述取代苯基可被选自C1到C4的烷基、卤素、羟基、氰基、羧酰胺基、硝基和C1到C4的烷氧基的一到三个基团所取代,其药学上可接受的盐是新的。这些化合物是有用的心理治疗剂,是有效的5-羟色胺(5-HT1)激动剂,可用于治疗抑郁症、焦虑症、饮食失调、肥胖症、药物滥用、集群头痛、偏头痛、疼痛、慢性阵发性半侧头痛和与缺乏5-羟色胺神经递质有关的其他疾病。这些化合物还可以用作中枢作用的降压剂和扩血管剂。
  • Indole derivatives
    申请人:Pfizer Inc
    公开号:US05607951A1
    公开(公告)日:1997-03-04
    Compounds of the formula ##STR1## wherein the substituents are as defined in the description and the pharmaceutically acceptable salts thereof are new. These compounds are useful psychotherapeutics and are potent serotonin (5-HT.sub.1) agonists and may be used in the treatment of depression, anxiety, eating disorders, obesity, drug abuse, cluster headache, migraine, pain, chronic paroxysmal hemicrania and headache associated with vascular disorders, and other disorders arising from deficient serotonergic neurotransmission. The compounds can also be used as centrally acting antihypertensives and vasodilators. A process for forming indoles by transition metal catalyzed cyclization of a dihalogenated intermediate.
    化合物的公式为##STR1##其中取代基如描述中所定义,以及其药学上可接受的盐是新的。这些化合物是有用的心理治疗药物,是有效的血清素(5-HT.sub.1)激动剂,并可用于治疗抑郁症、焦虑症、进食障碍、肥胖症、药物滥用、集群头痛、偏头痛、疼痛、慢性阵发性半侧头痛和与血管疾病相关的头痛以及因血清素能神经递质缺乏引起的其他疾病。这些化合物还可以用作中枢作用的降压药和扩血管剂。一种通过过渡金属催化的二卤代中间体环化形成吲哚的方法。
  • Synthesis and serotonergic pharmacology of the enantiomers of 3-[(N-methylpyrrolidin-2-yl)methyl]-5-methoxy-1H-indole: discovery of stereogenic differentiation in the aminoethyl side chain of the neurotransmitter serotonin
    作者:John E. Macor、James Blake、Carol B. Fox、Celeste Johnson、B. Kenneth Koe、Lorraine A. Lebel、Jean M. Morrone、Kevin Ryan、Anne W. Schmidt
    DOI:10.1021/jm00101a032
    日期:1992.11
  • INDOLE DERIVATIVES
    申请人:PFIZER INC.
    公开号:EP0592438B1
    公开(公告)日:1997-08-27
  • ETHERS AROMATIQUES DERIVES D'INDOLES COMME "5HT1-LIKE" LIGANDS
    申请人:PIERRE FABRE MEDICAMENT
    公开号:EP0782568B1
    公开(公告)日:2002-04-24
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