4-[[(2-chlorophenyl)imino](4-ethyl-1-piperazinyl)methyl]-benzoic acid methyl ester

• 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: 4-[[(2-chlorophenyl)imino](4-ethyl-1-piperazinyl)methyl]-benzoic acid methyl ester
• 化学式: C₂₁H₂₄ClN₃O₂
• 分子量: 385.893
• InChiKey: ABACXMSOOFDFCJ-ATJXCDBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  45.14
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-[[(2-chlorophenyl)imino](4-ethyl-1-piperazinyl)methyl]-benzoic acid methyl ester 在 sodium hydroxide 作用下， 生成
  参考文献：
  名称：

  哌嗪基苄am：对δ阿片受体的合成和亲和力。

  摘要：

  制备哌嗪基苯甲idine，并发现其与大鼠δ阿片受体结合。活性最高的化合物具有N，N-二乙基羧酰胺基和N-苄基哌嗪。其中最有效的是N，N-二乙基-4- [4-（苯基甲基）-1-哌嗪基] [2-（三氟甲基）苯基]亚氨基甲基]苯甲酰胺（27），大鼠的K（i）为1.22nM δ阿片受体和ca. 相对于mu阿片样物质亚型具有1000倍的选择性。

  DOI：

  10.1016/s0960-894x(01)00272-4
• 作为产物：
  描述：

  4-氯甲酰基苯甲酸甲酯 在 sodium hydroxide 、 水 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 生成 4-[[(2-chlorophenyl)imino](4-ethyl-1-piperazinyl)methyl]-benzoic acid methyl ester
  参考文献：
  名称：

  哌嗪基苄am：对δ阿片受体的合成和亲和力。

  摘要：

  制备哌嗪基苯甲idine，并发现其与大鼠δ阿片受体结合。活性最高的化合物具有N，N-二乙基羧酰胺基和N-苄基哌嗪。其中最有效的是N，N-二乙基-4- [4-（苯基甲基）-1-哌嗪基] [2-（三氟甲基）苯基]亚氨基甲基]苯甲酰胺（27），大鼠的K（i）为1.22nM δ阿片受体和ca. 相对于mu阿片样物质亚型具有1000倍的选择性。

  DOI：

  10.1016/s0960-894x(01)00272-4

文献信息

• Benzamidine derivatives
  申请人：——

  公开号：US20020123489A1

  公开（公告）日：2002-09-05

  Benzamidine derivatives are useful delta-opioid receptor modulators, agonists useful as analgesics and antagonists useful as immunosuppressants, antiinflammatory agents, agents for the treatment of neurological and psychiatric conditions, medicaments for drug and alcohol abuse, agents for treating gastritis and diarrhea, cardiovascular agents and agents for the treatment of respiratory diseases.

  苯甲酰胺衍生物是有用的δ阿片受体调节剂，作为镇痛剂有用的激动剂，作为免疫抑制剂有用的拮抗剂，抗炎药物，用于治疗神经系统和精神疾病的药物，用于药物和酒精滥用的药物，用于治疗胃炎和腹泻的药物，心血管药物和用于治疗呼吸系统疾病的药物。
• [EN] BENZAMIDINE DERIVATIVES<br/>[FR] DERIVES DE LA BENZAMIDINE
  申请人：ORTHO MCNEIL PHARM INC

  公开号：WO2002048122A2

  公开（公告）日：2002-06-20

  Benzamidine derivatives of the formula I are useful delta-opioid receptor modulators, agonists useful as analgesics and antagonists useful as immunosuppressants, antiinflammatory agents, agents for the treatment of neurological and psychiatric conditions medicaments for drug and alcohol abuse, agents for treating gastritis and diarrhea, cardiovascular agents and agents for the treatment of respiratory diseases. Wherein: X is a substituent selected from the group consisting of S and O; Z is a substituent selected from the group consisting of O(R5) and N(R6)(R7); the moiety -C(X)Z is substituted on the phenyl at the 3 or 4 position; n is an integer from 1 to 2; R1 is a substituent selected from the group consisting of hydrogen, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C1-6alkoxy(C1-6)alkyl, C1-6alkoxycarbonyl, C1-6alkyl(C1-6)alkoxycarbonyl, formyl, aryl, aryl(C1-6)alkyl, diaryl(C1-6)alkyl and heteroaryl(C1-6)alkyl; wherein aryl and heteroaryl are optionally substituted with one to three substituents independently selected from the group consisting of halogen, C1-4alkyl, C1-4alkoxy, amino, C1-4alkylamino, di(C1-4alkyl)amino, thrihaloC1-4alkyl and trihaloC1-4alkoxy; R2 and R3 are substituents independently selected from the group consisting of hydrogen and C1-6alkyl; Ar is aryl optionally substituted with one to three substituents selected from R4; R4 is a substituent selected from the group consisting of halogen, C1-6alkyl, C1-6alkoxy, aryl, aryl(C1-6)alkyl, heteroaryl, heteroaryl(C1-6)alkyl, amino, C1-6alkylamino, di(C1-6alkyl)amino, cyano, hydroxy, nitro, trihaloC1-4alkyl and trihaloC1-4alkoxy; alternatively, two R4 substituents may be fused together on adjacent carbon atoms to form a single fused moiety, wherein the moiety is selected from the group consisting of -(CH2)3-5- and -O(CH2)1-3O-; R5 is a substituent selected from C1-6alkyl; and R6 and R7 are substituents independently selected from the group consisting of hydrogen, C1-6alkyl, C2-6alkenyl, C3-7cycloalkyl, aryl and aryl(C1-6)alkyl, wherein cycloalkyl and aryl are optionally substituted with one to three substituents independently selected from the group consisting of halogen, C1-4alkyl,C2-4alkenyl, C1-4alkoxy, C3-7cycloalkyl, trihaloC1-3alkyl and trihaloC1-3alkoxy; alternatively, R6 and R7 may be fused together to form a single fused moiety, wherein the moiety is selected from the group consisting of -(CH2)3-5- and O(CH2)1-3O-; and pharmaceutically acceptable enantiomers, diastereomers and salts thereof.
• Piperazinyl benzamidines: Synthesis and affinity for the delta opioid receptor
  作者：Samuel O. Nortey、Ellen W. Baxter、Ellen E. Codd、Sui-Po Zhang、Allen B. Reitz

  DOI：10.1016/s0960-894x(01)00272-4

  日期：2001.7

  found to bind to the rat delta (delta) opioid receptor. The most active compounds had a N,N-diethylcarboxamido group and a N-benzyl piperazine. The most potent among these was N,N-diethyl-4-[4-(phenylmethyl)-1-piperazinyl][2-(trifluoromethyl)phenyl]iminomethyl]benzamide (27) with a 1.22nM K(i) for the rat delta opioid receptor and ca. 1000 x selectivity relative to the mu opioid subtype.

  制备哌嗪基苯甲idine，并发现其与大鼠δ阿片受体结合。活性最高的化合物具有N，N-二乙基羧酰胺基和N-苄基哌嗪。其中最有效的是N，N-二乙基-4- [4-（苯基甲基）-1-哌嗪基] [2-（三氟甲基）苯基]亚氨基甲基]苯甲酰胺（27），大鼠的K（i）为1.22nM δ阿片受体和ca. 相对于mu阿片样物质亚型具有1000倍的选择性。