(3-苯基丙基)-肼 | 3381-02-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (3-苯基丙基)-肼
• 英文名称: 3-phenylpropylhydrazine
• 英文别名: γ-Phenyl-propyl-hydrazin；1-Phenyl-3-hydrazinopropan；(3-Phenylpropyl)hydrazin；3-Phenylpropylhydrazin
• CAS: 3381-02-0
• 化学式: C₉H₁₄N₂
• 分子量: 150.224
• InChiKey: DJQQFWAGPAXTHH-UHFFFAOYSA-N

物化性质

• 沸点：
  -41-139 °C(Press: 8-9 Torr)
• 密度：
  0.993±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  (3-苯基丙基)-肼 在 盐酸 作用下， 以 二苯醚 、 乙醇 、 乙二醇甲醚 为溶剂， 反应 30.5h， 生成 5-amino-1-(3-phenylpropyl)-4-<3-(2-furyl)-1,2,4-triazol-5-yl>pyrazole
  参考文献：
  名称：

  Pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine Derivatives:  Potent and Selective A_2A Adenosine Antagonists

  摘要：

  A series of pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine derivatives (10a-o,q,r), bearing alkyl and aralkyl chains on positions 7 and 8, were synthesized in the attempt to obtain potent and selective antagonists for the A(2A) adenosine receptor subtype. The compounds were tested in binding and functional assays to evaluate their potency for the A(2A) compared with the A(1) adenosine receptor subtype. In binding studies in rat brain membranes, most of the compounds showed affinity for A(2A) receptors in the low nanomolar range with a different degree of A(2A) versus A(1) selectivity. Comparison of N-7 (10a-d,h-o)- and N-8 (10e-g)-substituted pyrazolo derivatives indicates that N-7 substitution decreases the A(1) affinity with the concomitant increase of A(2A) selectivity. Specifically, the introduction of a 3-phenylpropyl group at pyrazolo nitrogen in position 7 (101) increased significantly the A(2A) selectivity, being 210-fold, while the A(2A) receptor affinity remained high (K-i = 2.4 nM). With regards to the affinity for A(2A) receptors, also the compound 10n, bearing in the 7-position a beta-morpholin-4-ylethyl group, deserves attention (K-i = 5.6 nM) even though the A(2A) selectivity (84-fold) was not as high as that of 101. Conversely, the compound 10m (N-7-4-phenylbutyl derivative) showed a remarkable selectivity (A(1)/A(2A) ratio = 129) associated with lower A(2A) affinity (K-i = 21 nM). In functional studies, most of the compounds examined reversed 5'-(N-ethylcarbamoyl)adenosine-induced inhibition of rabbit platelet aggregation inhibition which is a biological response mediated by the A(2A) receptor subtype. The compounds are potent and selective A(2A) antagonists which can be useful to elucidate the pathophysiological role of this adenosine receptor subtype. These compounds deserve to be further developed to assess their potential for treatment of neurodegenerative disorders such as Parkinson's disease.

  DOI：

  10.1021/jm950746l
• 作为产物：
  描述：

  1-氯-3-苯基丙烷 在 肼 作用下， 生成 (3-苯基丙基)-肼
  参考文献：
  名称：

  Jensen,K.A. et al., Acta Chemica Scandinavica (1947), 1961, vol. 15, p. 1109 - 1123

  摘要：

  DOI：
• 作为试剂：
  描述：

  (2S,4R)-4-(2-chloro-benzenesulfonyl)-1-(3-oxo-thiobutyryl)-pyrrolidine-2-carboxylic acid methyl ester 、 (3-苯基丙基)-肼 在 (3-苯基丙基)-肼 作用下， 反应 192.0h， 以3381-02-0) to give the title compound as yellow oil的产率得到(2S,4R)-4-(2-Chlorophenylsulfonyl)-1-(3-methyl-1-(3-phenylpropyl)-1H-pyrazol-5-yl)pyrrolidine-2-carboxylic Acid Methyl Ester
  参考文献：
  名称：

  Proline derivatives

  摘要：

  本发明涉及一种式为(I)的化合物，其中A，R1-R6在说明书和权利要求书中定义。式(I)化合物可用作药物。

  公开号：

  US08163793B2

文献信息

• Discovery of 1,5-Diphenylpyrazole-3-Carboxamide Derivatives as Potent, Reversible, and Selective Monoacylglycerol Lipase (MAGL) Inhibitors
  作者：Mojgan Aghazadeh Tabrizi、Pier Giovanni Baraldi、Stefania Baraldi、Emanuela Ruggiero、Lucia De Stefano、Flavio Rizzolio、Lorenzo Di Cesare Mannelli、Carla Ghelardini、Andrea Chicca、Margherita Lapillo、Jürg Gertsch、Clementina Manera、Marco Macchia、Adriano Martinelli、Carlotta Granchi、Filippo Minutolo、Tiziano Tuccinardi

  DOI：10.1021/acs.jmedchem.7b01845

  日期：2018.2.8

  compound 26 showed to be a potent MAGL inhibitor (IC50 = 0.51 μM, Ki = 412 nM) with a good selectivity versus fatty acid amide hydrolase (FAAH), α/β-hydrolase domain-containing 6 (ABHD6), and 12 (ABHD12). Interestingly, this compound also possesses antiproliferative activities against two different cancer cell lines and relieves the neuropathic hypersensitivity induced in vivo by oxaliplatin.

  单酰基甘油脂酶（MAGL）是一种丝氨酸水解酶，在内源性大麻素神经递质2-花生四烯酸甘油酯的降解中起重要作用，这与许多生理过程有关。除了可能将MAGL抑制剂用作抗炎药，抗伤害感受药和抗癌药外，由于不可逆地抑制该酶所引起的不良作用，它们的应用也遇到了障碍。可逆的MAGL抑制剂的可能用途直到最近才被研究，主要是由于缺乏具有有效的可逆抑制活性的已知化合物。在这项工作中，我们报告了一系列新的可逆MAGL抑制剂。其中，化合物26被证明是有效的MAGL抑制剂（IC 50 = 0.51μM ，与脂肪酸酰胺水解酶（FAAH），含α/β水解酶结构域的6（ABHD6）和12（ABHD12）相比，K i = 412 nM）具有良好的选择性。有趣的是，该化合物还具有针对两种不同癌细胞系的抗增殖活性，并减轻了奥沙利铂在体内引起的神经性超敏反应。
• NOVEL PROLINE DERIVATIVES
  申请人：Sánchez Rubén Alvarez

  公开号：US20100267722A1

  公开（公告）日：2010-10-21

  The invention relates to a compound of formula (I) wherein A, R 1 -R 6 are as defined in the description and in the claims. The compound of formula (I) can be used as a medicament.

  这项发明涉及一种化合物，其化学式为（I），其中A，R1-R6如描述和权利要求中所定义。化合物的化学式（I）可用作药物。
• Design, Synthesis, and Biological Evaluation of C⁹- and C²-Substituted Pyrazolo[4,3-<i>e</i>]-1,2,4-triazolo[1,5-<i>c</i>]pyrimidines as New A_2A and A₃ Adenosine Receptors Antagonists
  作者：Pier Giovanni Baraldi、Francesca Fruttarolo、Mojgan Aghazadeh Tabrizi、Delia Preti、Romeo Romagnoli、Hussein El-Kashef、Allan Moorman、Katia Varani、Stefania Gessi、Stefania Merighi、Pier Andrea Borea

  DOI：10.1021/jm021023m

  日期：2003.3.1

  C(2)-substituted pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines to represent an extension of structure-activity relationship work on this class of tricyclic compounds. The introduction of a substituent at 9 position of the tricyclic antagonistic structure led to retention of receptor affinity but a loss of selectivity in respect to the lead compounds b, N(8)-substituted-pirazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines-N(5)-urea

  在过去的几年中，我们小组一直致力于A（2A）和A（3）腺苷受体拮抗剂的开发，从而导致了SCH58261（5-氨基-7-（2-苯乙基）-2-（ 2-furyl）pyrazolo [4,3-e] -1,2,4-triazolo [1,5-c] pyrimi dine，61），对A（2A）受体亚型和N（8 ）-取代的吡唑并[4,3-e] -1,2,4-三唑并[1,5-c]嘧啶-N（5）-脲或酰胺（MRE系列，b），对人A的选择性很高（3）腺苷受体亚型。我们现在描述一系列由C（9）-和C（2）取代的吡唑并[4,3-e] -1,2,4-三唑并[1,5-c]嘧啶，以代表结构的扩展-这类三环化合物之间存在活性关系。在三环拮抗结构的9位上引入取代基导致保留受体亲和力，但相对于先导化合物b，N（8）-取代的吡唑并[4,3-e] -1，失去了选择性， 2,4-三唑并[1,5-c]嘧啶-N（5）-脲或-酰胺。受
• [EN] CHALCONE-UREA DERIVATIVES AS INSULIN SENSORS<br/>[FR] DÉRIVÉS DE CHALCONE-URÉE UTILISÉS EN TANT QUE CAPTEURS D'INSULINE
  申请人：AGENCY SCIENCE TECH & RES

  公开号：WO2015080665A1

  公开（公告）日：2015-06-04

  The invention relates to compounds of formula (I) or derivatives, tautomeric forms, stereoisomers, polymorphs, hydrates, solvates, pharmaceutically acceptable salts, pharmaceutical compositions, metabolites or prodrugs thereof, in which the substituents are as defined in the specification. These compounds may be useful as insulin sensors; in insulin secretion studies and as probes for insulin detection.

  本发明涉及式(I)化合物或其衍生物、互变异构体、立体异构体、多晶型、水合物、溶剂物、药学上可接受的盐、药物组合物、代谢物或其前药物。其中，取代基在说明书中定义。这些化合物可以用作胰岛素传感器，用于胰岛素分泌研究和作为胰岛素检测的探针。
• 2-(3-Phenylpropyl)hydrazines, intermediates in and a process for the preparation thereof, and their use as medicaments
  申请人：HOECHST-ROUSSEL PHARMACEUTICALS INCORPORATED

  公开号：EP0545425A1

  公开（公告）日：1993-06-09

  The present invention relates to 2-[3-phenyl-3-(phenoxy)propyl]hydrazines of formula I wherein R is hydrogen or loweralkyl; R₁ is hydrogen, loweralkyl, arylloweralkyl, a group of the formula wherein R₂ is loweralkyl, or a group of the formula wherein R₃ is hydrogen, loweralkyl, aryl, or arylloweralkyl; X and Y are hydrogen, loweralkyl, loweralkoxy, halogen, or trifluoromethyl; m and n are independently 1 or 2; the optical isomers thereof; or the pharmaceutically acceptable acid addition salts thereof, which are useful for treating personality disorders such as obsessive compulsive disorders. This invention relates further to intermediates in and a process for the preparation of the compounds of formula I.

  本发明涉及式 I 的 2-[3-苯基-3-(苯氧基)丙基]肼 其中 R 是氢或低级烷基；R₁ 是氢、低级烷基、芳基低级烷基、式中的基团 其中 R₂ 是低级烷基，或一个式基团 其中 R₃ 是氢、低级烷基、芳基或芳基低级烷基；X 和 Y 是氢、低级烷基、低级烷氧基、卤素或三氟甲基；m 和 n 独立地为 1 或 2；其光学异构体；或其药学上可接受的酸加成盐，可用于治疗强迫症等人格障碍。 本发明还涉及式 I 化合物的中间体和制备工艺。