1-(4-benzylpiperazin-1-yl)-3-phenyl-propan-2-one | 167273-25-8

• 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: 1-(4-benzylpiperazin-1-yl)-3-phenyl-propan-2-one
• 英文别名: 1-(4-benzylpiperazin-1-yl)-3-phenylpropan-2-one
• CAS: 167273-25-8
• 化学式: C₂₀H₂₄N₂O
• 分子量: 308.423
• InChiKey: KBSWCIVFXUTBOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-benzylpiperazin-1-yl)-3-phenyl-propan-2-one 在 一水合肼 、 N,N'-羰基二咪唑 、 lithium hexamethyldisilazane 作用下， 以 甲醇 为溶剂， 反应 2.25h， 生成 1-benzyl-4-(5-methyl-4-phenyl-1H-pyrazol-3-ylmethyl)-piperazine
  参考文献：
  名称：

  Substituted pyrazoles as novel selective ligands for the human dopamine D 4 receptor

  摘要：

  Two novel series of 3-(heterocyclylmethyl)pyrazoles have been synthesised and evaluated as ligands for the human dopamine D-4 receptor. Compounds in series I (exemplified by 8k) have a phenyl ring joined to the 4-position of the pyrazole while those in series II (exemplified by 15j) have a 5-phenyl ring linked by a saturated chain to the 4-position of the pyrazole. Both series supplied compounds with excellent affinity for the human D-4 and good selectivity over other dopamine receptors. Excellent selectivity over calcium, sodium, and potassium ion channels was also achieved. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00134-5
• 作为产物：
  描述：

  1-苄基-4-Boc-哌嗪 在 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 1-(4-benzylpiperazin-1-yl)-3-phenyl-propan-2-one
  参考文献：
  名称：

  Substituted pyrazoles as novel selective ligands for the human dopamine D 4 receptor

  摘要：

  Two novel series of 3-(heterocyclylmethyl)pyrazoles have been synthesised and evaluated as ligands for the human dopamine D-4 receptor. Compounds in series I (exemplified by 8k) have a phenyl ring joined to the 4-position of the pyrazole while those in series II (exemplified by 15j) have a 5-phenyl ring linked by a saturated chain to the 4-position of the pyrazole. Both series supplied compounds with excellent affinity for the human D-4 and good selectivity over other dopamine receptors. Excellent selectivity over calcium, sodium, and potassium ion channels was also achieved. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00134-5

文献信息

• Isoxazole and pyrazole derivatives as dopamine receptor subtype ligands
  申请人：Merck, Sharp & Dohme, Ltd.

  公开号：US05684006A1

  公开（公告）日：1997-11-04

  A class of substituted isoxazole and pyrazole derivatives of formula (I), or a salt thereof of or a prodrug thereof, wherein the broken circle represents two non-adjacent double bonds whereby the five-membered ring containing X and Y is aromatic; one of X and Y represents nitrogen, and the other of X and Y represents oxygen or N--R.sup.5 ; R.sup.1 represents hydrogen, C.sub.1-6 alkyl or trifluoromethyl; R.sup.2 and R.sup.3 independently represent hydrogen, hydrocarbon, a heterocyclic group, halogen, cyano, trifluoromethyl, nitro, --OR.sup.a, --SR.sup.a, --SOR.sup.a, --SO.sub.2 R.sup.a, --SO.sub.2 NR.sup.a R.sup.b, --NR.sup.a R.sup.a, --NR.sup.a CO.sub.2 R.sup.b, --COR.sup.a, --CO.sub.2 R.sup.a or --CONR.sup.a R.sup.b, R.sup.4 represents hydrocarbon or a heterocyclic group; R.sup.5 represents hydrogen or C.sub.1-6 alkyl; and R.sup.a and R.sup.b independently represent hydrogen, hydrocarbon or a heterocyclic group, are ligands for dopamine receptor subtypes within the body and are therefore useful in the treatment and/or prevention of disorders of the dopamine system, in particular schizophrenia. ##STR1##

  一类取代的异苯并噁唑和吡唑衍生物，其化学式为（I），或其盐或前药，其中断圆圈代表两个非相邻的双键，五元环含有X和Y是芳香的; X和Y中的一个代表氮，另一个代表氧或N-R.sup.5; R.sup.1代表氢，C.sub.1-6烷基或三氟甲基; R.sup.2和R.sup.3分别代表氢，碳氢化合物，杂环基团，卤素，氰基，三氟甲基，硝基，-OR.sup.a，-SR.sup.a，-SOR.sup.a，-SO.sub.2R.sup.a，-SO.sub.2NR.sup.aR.sup.b，-NR.sup.aR.sup.a，-NR.sup.aCO.sub.2R.sup.b，-COR.sup.a，-CO.sub.2R.sup.a或 -CONR.sup.aR.sup.b，R.sup.4代表碳氢化合物或杂环基团; R.sup.5代表氢或C.sub.1-6烷基; R.sup.a和R.sup.b分别代表氢，碳氢化合物或杂环基团，是体内多巴胺受体亚型的配体，因此在治疗和/或预防多巴胺系统疾病，特别是精神分裂症方面有用。##STR1##
• [EN] ISOXAZOLE AND PYRAZOLE DERIVATIVES AS DOPAMINE RECEPTOR SUBTYPE LIGANDS<br/>[FR] DERIVES D'ISOXAZOLE ET DE PYRAZOLE EN TANT QUE LIGANDS DE SOUS-TYPES DE RECEPTEURS DE LA DOPAMINE
  申请人：MERCK SHARP & DOHME LIMITED

  公开号：WO1995014672A1

  公开（公告）日：1995-06-01

  (EN) A class of substituted isoxazole and pyrazole derivatives of formula (I), or a salt thereof or a prodrug thereof, wherein the broken circle represents two non-adjacent double bonds whereby the five-membered ring containing X and Y is aromatic; one of X and Y represents nitrogen, and the other of X and Y represents oxygen or N-R5; R1 represents hydrogen, C1-6 alkyl or trifluoromethyl; R2 and R3 independently represent hydrogen, hydrocarbon, a heterocyclic group, halogen, cyano, trifluoromethyl, nitro, -ORa, -SRa, -SORa, -SO2Ra, -SO2NRaRb, -NRaRb, -NRaCORb, -NRaCO2Rb, -CORa, -CO2Ra or -CONRaRb; R4 represents hydrocarbon or a heterocyclic group; R5 represents hydrogen or C1-6 alkyl; and Ra and Rb independently represent hydrogen, hydrocarbon or a heterocyclic group, are ligands for dopamine receptor subtypes within the body and are therefore useful in the treatment and/or prevention of disorders of the dopamine system, in particular schizophrenia.(FR) L'invention se rapporte à une classe de dérivés d'isoxazole et de pyrazole substitués de la formule (I), ou à un sel de ces dérivés ou à un promédicament les contenant. Dans cette formule, le cercle en pointillé représente deux doubles liaisons non adjacentes grâce auxquelles le noyau à cinq éléments contenant X et Y est aromatique; un des éléments X et Y représente azote, et l'autre représente oxygène ou N-R5; R1 représente hydrogène, alkyle C1-6 ou trifluorométhyle; R2 et R3 représentent indépendamment hydrogène, hydrocarbure, un groupe hétérocyclique, halogène, cyano, trifluorométhyle, nitro, -ORa, -SRa, -SORa, -SO2Ra, -SO2NRaRb, -NRaRb, -NRaCORb, -NRaCO2Rb, -CORa, -CO2Ra ou -CONRaRb; R4 représente hydrocarbure ou un groupe hétérocyclique; R5 représente hydrogène ou alkyle C1-6; et Ra et Rb représentent indépendamment hydrogène, hydrocarbure ou un groupe hétérocyclique. Ces dérivés sont des ligands de sous-types de récepteurs de la dopamine agissant dans le corps humain et sont par conséquent utiles dans le traitement et/ou la prévention de troubles du système dopamine, notamment de la schizophrénie.

  本发明涉及一类亚恶唑和吡唑衍生物，其通式为(I)，或这些衍生物的盐或前药。其中虚线圆环代表两个非相邻双键，使得含有X和Y的五元环是芳香族的；X和Y之一代表氮原子，另一者代表氧原子或N-R5；R1表示氢、C1-6烷基或三氟甲基；R2和R3各自独立地表示氢、烃类、杂环基团、卤素、氰基、三氟甲基、硝基、-ORa、-SRa、-SORa、-SO2Ra、-SO2NRaRb、-NRaRb、-NRaCORb、-NRaCO2Rb、-CORa、-CO2Ra或-CONRaRb；R4表示烃类或杂环基团；R5表示氢或C1-6烷基；Ra和Rb各自独立地表示氢、烃类或杂环基团。这些衍生物是体内多巴胺受体亚型的配体，因此可用于治疗和/或预防多巴胺系统相关的疾病，特别是精神分裂症。
• ISOXAZOLE AND PYRAZOLE DERIVATIVES AS DOPAMINE RECEPTOR SUBTYPE LIGANDS
  申请人：MERCK SHARP & DOHME LTD.

  公开号：EP0730582A1

  公开（公告）日：1996-09-11
• US5684006A
  申请人：——

  公开号：US5684006A

  公开（公告）日：1997-11-04
• Substituted pyrazoles as novel selective ligands for the human dopamine D 4 receptor
  作者：Sylvie Bourrain、Ian Collins、Joseph G. Neduvelil、Michael Rowley、Paul D. Leeson、Smita Patel、Shil Patel、Frances Emms、Rosemarie Marwood、Kerry L. Chapman、Alan E. Fletcher、Graham A. Showell

  DOI：10.1016/s0968-0896(98)00134-5

  日期：1998.10

  Two novel series of 3-(heterocyclylmethyl)pyrazoles have been synthesised and evaluated as ligands for the human dopamine D-4 receptor. Compounds in series I (exemplified by 8k) have a phenyl ring joined to the 4-position of the pyrazole while those in series II (exemplified by 15j) have a 5-phenyl ring linked by a saturated chain to the 4-position of the pyrazole. Both series supplied compounds with excellent affinity for the human D-4 and good selectivity over other dopamine receptors. Excellent selectivity over calcium, sodium, and potassium ion channels was also achieved. (C) 1998 Elsevier Science Ltd. All rights reserved.