4-(4-diphenyl-methyl-1-piperazinyl)butylamine | 101620-10-4

• 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-(4-diphenyl-methyl-1-piperazinyl)butylamine
• 英文别名: 4-(4-benzhydrylpiperazin-1-yl)butan-1-amine；1-(4-aminobutyl)-4-(diphenylmethyl)piperazine
• CAS: 101620-10-4
• 化学式: C₂₁H₂₉N₃
• 分子量: 323.481
• InChiKey: NSMZTYPXRYZENQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  32.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-diphenyl-methyl-1-piperazinyl)butylamine 以61%的产率得到3-t-Butoxycarbonyl-4(R)-[4-(4-diphenylmethyl-1-piperazinyl) butylcarbamoyl]-2-(3-pyridyl)thiazolidine
  参考文献：
  名称：

  Thiazolidinecarboxylic acid amide derivatives and their therapeutic uses

  摘要：

  具有联合抗过敏和抗哮喘活性的噻唑烷羧酸酰胺，具有对血小板活化因子的拮抗活性，其一般结构式如下：

  公开号：

  US05470851A1
• 作为产物：
  描述：

  二苯甲基哌嗪 在 potassium carbonate 、 一水合肼 、 sodium iodide 作用下， 以 乙醇 、 丁酮 为溶剂， 反应 6.5h， 生成 4-(4-diphenyl-methyl-1-piperazinyl)butylamine
  参考文献：
  名称：

  Acrylamide derivatives as antiallergic agents. I. Synthesis and structure-activity relationships of N-((4-substituted 1-piperazinyl)alkyl)-3-(aryl and heteroaryl)acrylamides.

  摘要：

  一系列新的丙烯酰胺衍生物（7-10）被合成。对这些化合物的抗过敏活性进行了评估，并考察了它们的结构-活性关系。化合物10d，即N[4-(4-二苯甲基-1-哌嗪基)丁基]3-(3-吡啶基)丙烯酰胺，在口服给药的大鼠被动皮肤过敏反应（PCA）测试中显示出与酮替芬相当或更优越的抗过敏活性。与酮替芬不同，10d在体外对5-脂氧合酶的抑制活性比咖啡酸更强，而其体外抗组胺活性则弱于酮替芬。此外，它对大鼠肥大细胞释放组胺的抑制活性约为色甘酸二钠（DSCG）的三分之二。化合物10d是一种有前途的多种过敏性疾病治疗药物。

  DOI：

  10.1248/cpb.37.100
• 作为试剂：
  描述：

  3-(6-methyl-3-pyridyl)acrylic acid 、 4-(4-diphenyl-methyl-1-piperazinyl)butylamine 在 4-(4-diphenyl-methyl-1-piperazinyl)butylamine 作用下， 以70的产率得到N-[3-(6-methyl-pyridin-3-yl)acryloyl]-4-(4-diphenylmethyl-1-piperazinyl)butylamine
  参考文献：
  名称：

  J. Med. Chem. 1989, 32, 583-593

  摘要：

  DOI：

文献信息

• Synthesis and histamine H1-receptor antagonist activity of 4-(diphenylmethyl)-1-piperazine derivatives with a terminal heteroaryl or cycloalkyl amide fragment
  作者：A Orjales、JC Gil-Sánchez、L Alonso-Cires、L Labeaga、R Mosquera、A Berisa、M Ucelay、A Innerárity、R Corcóstegui

  DOI：10.1016/0223-5234(96)83975-4

  日期：1996.1

  New 4-(diphenylmethyl)-1-piperazine derivatives with a terminal heteroaryl or cycloalkyl amide fragment were synthesized and evaluated for their antihistaminic, anticholinergic and antiallergic activities. Tested compounds were found to be moderate to potent in vitro (guinea-pig ileum) histamine H(1)-receptor antagonists. Derivatives with a four methylene chain (1e-1h) were as potent in vivo (capillary

  合成了具有末端杂芳基或环烷基酰胺片段的新的4-（二苯甲基）-1-哌嗪衍生物，并对其抗组胺，抗胆碱能和抗过敏活性进行了评估。发现测试的化合物是中等至有效的体外（豚鼠回肠）组胺H（1）-受体拮抗剂。具有四个亚甲基链（1e-1h）的衍生物在体内（大鼠的毛细血管通透性）与西替利嗪一样有效。发现杂芳基衍生物1e和1h是最活跃的试剂。这些化合物显示仅弱体外（豚鼠回肠）毒蕈碱M（3）-受体拮抗剂活性。在阻止化合物48/80诱导的组胺从大鼠腹膜肥大细胞释放方面，化合物1e和1g的效力比酮替芬高约100倍。导数1e 1f和1h不会改变大鼠口服100 mg / kg时的自发运动活动。已选择化合物1e进行进一步研究。
• Synthesis, Structure−Activity Relationship, and Mode-of-Action Studies of Antimalarial Reversed Chloroquine Compounds
  作者：Steven J. Burgess、Jane X. Kelly、Shawheen Shomloo、Sergio Wittlin、Reto Brun、Katherine Liebmann、David H. Peyton

  DOI：10.1021/jm1006484

  日期：2010.9.9

  moiety and a resistance reversal-like moiety, can overcome chloroquine resistance in P. falciparum (Burgess, S. J.; Selzer, A.; Kelly, J. X.; Smilkstein, M. J.; Riscoe, M. K.; Peyton, D. H. J. Med. Chem. 2006, 49, 5623. Andrews, S.; Burgess, S. J.; Skaalrud, D.; Kelly, J. X.; Peyton, D. H. J. Med. Chem. 2010, 53, 916). Here, we present an investigation into the structure−activity relationship of the RCQ

  我们先前已经证明了“反向氯喹（RCQ）”分子，的氯喹等构成部分和耐药性逆转样部分，可以克服在氯喹抗性的恶性疟原虫（伯吉斯，SJ；塞尔泽，A.；凯利，JX；斯米尔克斯坦，MJ；里斯科，MK；佩顿，卫生署 J. 医学。化学 2006年，49，5623。安德鲁斯，S。伯吉斯，SJ；斯卡尔鲁德，D.；凯利，JX；佩顿，卫生署 J. 医学。化学 2010 , 53 , 916)。在这里，我们对 RCQ 结构的构效关系进行了研究，从而产生了一种具有良好体外和体内抗疟活性的口服活性分子。我们还提供了作用方式的证据，表明 RCQ 分子以类似于氯喹的方式抑制寄生虫消化液泡中血红素的形成。
• .omega.-(3-pyridyl)alkenamide derivatives and anti-allergenic
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：US04778796A1

  公开（公告）日：1988-10-18

  Compounds of the formula: ##STR1## wherein X is alkylene or --(CR.sub.6 .dbd.CR.sub.7).sub.r -- wherein R.sub.6 is H, alkyl or phenyl, R.sub.7 is H, alkyl, cyano or phenyl, and r is 1 or 2; A is alkylene or alkylene interrupted by at least one double bond; R.sub.1 is H, halogen, alkyl, alkoxy, alkylthio, cycloalkyloxy, cycloalkylthio, alkoxycarbonyl, carboxy, phenyl, phenoxy, phenylthio, 3-pyridyloxy or 3-pyridylthio; R.sub.2 is H, hydroxy, alkanoyloxy or alkoxycarbonyloxy, or adjacent R.sub.1 and R.sub.2 may combine to form tetramethylene or --CH.sub.2 OCR.sub.8 R.sub.9 O-- (R.sub.8 and R.sub.9 are alkyl); R.sub.3 is H, alkyl or hydroxyalkyl; R.sub.4 is H or alkyl; R.sub.5 is phenyl, heteroaryl or --(CH.sub.2).sub.m --CHR.sub.10 R.sub.11 (R.sub.10 is H or phenyl, R.sub.11 is phenyl or pyridyl and m is 0 to 2); p is 0 or 1; and q is 2 or 3; the phenyl group or moiety being optionally substituted, and a salt thereof, process for the preparation thereof, and pharmaceutical composition containing the same. Said compounds and salts thereof show excellent antiallergic activity mainly through 5-lipoxygenase inhibiting activity, antihistamine activity and/or inhibitory activity against chemical mediator release and useful for treatment of allergic diseases.

  该公式化合物为：其中X为烷基或--(CR6.dbd.CR7)r--，其中R6为H、烷基或苯基，R7为H、烷基、氰基或苯基，r为1或2；A为烷基或至少有一个双键中断的烷基；R1为H、卤素、烷基、烷氧基、烷基硫基、环烷氧基、环烷硫基、烷氧羰基、羧基、苯基、苯氧基、苯硫基、3-吡啶氧基或3-吡啶硫基；R2为H、羟基、烷酰氧基或烷氧羰氧基，或相邻的R1和R2可结合形成四亚甲基或--CH2OCR8R9O--（R8和R9为烷基）；R3为H、烷基或羟基烷基；R4为H或烷基；R5为苯基、杂环芳基或--(CH2)m--CHR10R11（R10为H或苯基，R11为苯基或吡啶基，m为0至2）；p为0或1；q为2或3；苯基或基团可选择性地被取代，以及其盐，以及制备方法和含有该化合物的药物组合物。所述化合物及其盐主要通过5-脂氧合酶抑制活性、抗组胺活性和/或抑制化学介质释放活性表现出优异的抗过敏活性，对于治疗过敏性疾病具有用处。
• Derivatives of 1-diphenylmethyl piperazine and their use as
  申请人：Laboratorios Del Dr. Esteve, S. A.

  公开号：US05166205A1

  公开（公告）日：1992-11-24

  The present invention relates to novel derivatives of 1-diphenylmethyl piperazinyl, characterized in that they correspond to the general formula I, and their therapeutically acceptable salts, ##STR1## in which: R.sub.1 and R.sub.2, equal or different, represent a hydrogen atom, a halogen, a lower alkyl radical, a hydroxy radical, an alkoxy radical, an alkyl carboxylate radical, an aryl or substituted aryl radical, n may have the values 2 to 4, X, Y, Z and W, equal or different, represent a nitrogen atom or a carbon atom linked to a hydrogen atom, a halogen or to another alkyl, aryl, carboxyalkyl, carbonyl, hydroxyl, sulfonyl and alkylsulfonyl radical. The present invention also relates to the process of preparing these compounds and their use for the manufacture of medicaments intended for prophylaxis and for the treatment of various allergic disorders caused by histamine.

  本发明涉及1-二苯甲基哌嗪新型衍生物，其特征在于它们符合通式I，并且它们的治疗接受的盐，其中：R1和R2，相等或不同，代表氢原子、卤素、较低的烷基基团、羟基基团、烷氧基团、烷基羧酸酯基团、芳基或取代的芳基，n的值可以是2到4，X、Y、Z和W，相等或不同，代表与氢原子、卤素或另一个烷基、芳基、羧基烷基、羰基、羟基、磺酰基和烷基磺酰基基团连接的氮原子或碳原子。本发明还涉及制备这些化合物的过程以及它们用于制造用于预防和治疗由组胺引起的各种过敏性疾病的药物。
• Acrylamide derivatives as antiallergic agents. III. Synthesis and structure-activity relationships of N-(4-(4-diphenylmethyl-1-piperazinyl)butyl)- and N-(4-(4-diphenylmethylene-1-piperidyl)butyl)-3-heteroacrylacrylamides.
  作者：Yoshinori NISHIKAWA、Tokuhiko SHINDO、Katsumi ISHII、Hideo NAKAMURA、Tatsuya KON、Hitoshi UNO

  DOI：10.1248/cpb.37.684

  日期：——

  A new series of 3-heteroarylacrylamides 2 and 4 was prepared and the inhibitory activities against the rat passive cutaneous anaphylaxis (PCA) reaction and the enzyme 5-lipoxygenase (5-LO) were tested. Most of the compounds exhibited an anti-PCA activity superior to or equivalent to ketotifen and had a 5-LO inhibitory activity. The 3-heteroarylacrylamide derivatives including 3-(3-pyridyl)acrylamides represent a new structural class of compound that exhibits not only an in vivo anti-PCA activity but also an in vitro 5-LO ingibitory activity.

  制备了一系列新的 3-杂芳基丙烯酰胺 2 和 4，并测试了它们对大鼠被动皮肤过敏性休克（PCA）反应和 5-脂氧合酶（5-LO）的抑制活性。大多数化合物的抗 PCA 活性优于或相当于酮替芬，并具有 5-LO 抑制活性。3-teroarylacrylamide 衍生物（包括 3-(3-吡啶基)丙烯酰胺）代表了一类结构新颖的化合物，不仅具有体内抗PCA 活性，而且还具有体外 5-LO 摄取活性。