1-(2-Chloro-5-trifluoromethyl-phenyl)-piperazine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-(2-Chloro-5-trifluoromethyl-phenyl)-piperazine
• 英文别名: 1-[2-Chloro-5-(trifluoromethyl)phenyl]piperazine
• 化学式: C₁₁H₁₂ClF₃N₂
• mdl: MFCD05182256
• 分子量: 264.678
• InChiKey: YJEUNFQPKZSQEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-Chloro-5-trifluoromethyl-phenyl)-piperazine 、 1-碘代丙烷 在 title compound 作用下， 生成 1-(2-Chloro-5-trifluoromethyl-phenyl)-4-propyl-piperazine
  参考文献：
  名称：

  Modulators of dopamine neurotransmission

  摘要：

  公式（1）中的新取代的4-苯基N-烷基哌嗪和4-苯基N-烷基哌啶化合物，其中X为N，CH或C，但当化合物在虚线处具有双键时，X只能为C；R1为CF3，OSO2CF3，OSO2CH3，SOR7，SO2R7，COR7，CN，OR3，NO2，CONHR3，3-噻吩，2-噻吩，3-呋喃，2-呋喃，F，Cl，Br或I；R2为F，Cl，Br，I，CN，CF3，CH3，OCH3，OH和NH2；R3和R4独立地为H或C1-C4烷基；R5为C1-C4烷基，烯丙基，CH2SCH3，CH2CH2OCH3，CH2CH2CH2F，CH2CF3，3,3,3-三氟丙基，4,4,4-三氟丁基或-(CH2)-R6；R6为C3-C6环烷基，2-四氢呋喃或3-四氢呋喃；R7为C1-C3烷基，CF3或N（R4）2，并公开了其药学上可接受的盐。还公开了包含上述化合物的制药组合物和使用上述化合物治疗中枢神经系统疾病的方法。

  公开号：

  US20030004169A1
• 作为产物：
  描述：

  3-[2-[2-chloro-5-(trifluoromethyl)anilino]ethyl]-1,3-oxazolidin-2-one 在 氢溴酸 作用下， 生成 1-(2-Chloro-5-trifluoromethyl-phenyl)-piperazine
  参考文献：
  名称：

  使用2-恶唑烷酮作为潜在的氮丙啶等效物。三，N-取代的哌嗪的制备

  摘要：

  由各种取代的2-恶唑烷酮衍生物3制备了许多N-芳基和N-烷基取代的哌嗪1。该方法包括在冰醋酸中用HBr处理3，然后在醇溶剂中加热所得的开环盐5。通过结晶分离出哌嗪1a-1q，产率为23-91％。

  DOI：

  10.1016/0040-4039(94)85306-1

文献信息

• HETEROCYCLIC DERIVATIVES AS INHIBITORS OF STEAROYL-COENZYME A DELTA-9 DESATURASE
  申请人：Isabel Elise

  公开号：US20110301143A1

  公开（公告）日：2011-12-08

  Heterocyclic compounds of structural formula (I), or a pharmaceutically acceptable salt thereof, wherein W is a R 1 — substituted heteroaryl, R 1 is an heteroaryl ring substituted with an ester or carboxylic acid containing radical, X-T is N—CR 5 R 6 , C═CR 5 or CR 13 —CR 5 R 6 , Y is a bond or —C(O)—, a and b represent an integer selected from 1 to 4, and Ar is an optionally substituted phenyl or naphtyl, are inhibitors of stearoyl-coenzyme A delta-9 desaturase (SCD) The heterocyclic compounds are useful for the prevention and treatment of conditions related to abnormal lipid synthesis and metabolism, including cardiovascular disease, atherosclerosis, obesity, diabetes, neurological disease, Metabolic Syndrome, insulin resistance, cancer, liver steatosis, and non-alcoholic steatohepatitis.

  结构式（I）的杂环化合物，或其药学上可接受的盐，其中W是R1-取代的杂芳基，R1是取代有酯基或羧基的杂芳基环，X-T是N—CR5R6，C═CR5或CR13—CR5R6，Y是键或—C(O)—，a和b代表选自1到4的整数，Ar是可选择取代的苯基或萘基，是硬脂酰辅酶A 9-脱饱和酶（SCD）的抑制剂。这些杂环化合物对于预防和治疗与异常脂质合成和代谢有关的疾病非常有用，包括心血管疾病、动脉粥样硬化、肥胖症、糖尿病、神经系统疾病、代谢综合征、胰岛素抵抗、癌症、肝脂肪变性和非酒精性脂肪肝。
• Indazole compound and pharmaceutical use thereof
  申请人：Takemiya Akihiro

  公开号：US20070173537A1

  公开（公告）日：2007-07-26

  The present invention can provide a cancer treatment drug containing, as an active ingredient, a substance selected from the group consisting of an indazole compound of the following formula (I), a pharmaceutically acceptable salt, a hydrate, a water adduct and a solvate:

  本发明可以提供一种癌症治疗药物，其包含以下公式（I）中的吲唑化合物、药用可接受盐、水合物、水加合物和溶剂化物等物质中所选的一种作为活性成分：
• 4-Phenylpiperidine derivatives as modulators of dopamine neurotransmission
  申请人：A. Carlsson Research AB

  公开号：EP1419773A2

  公开（公告）日：2004-05-19

  New substituted 4-(phenyl-N-alkyl)-piperidine compounds of Formula 1: wherein X is CH; R1 is CF3, OSO2CF3, OSO2CH3, SOR7, SO2R7, COR7, CN, OR3, NO2, CONHR3, 3-thiophene, 2-thiophene, 3-furane, 2-furane, F, Cl, Br, or I; R2 is F, Cl, Br, I, CN, CF3, CH3, OCH3, OH, and NH2; R3 and R4 are H; R5 is a C1-C4 alkyl, an allyl, CH2SCH3, CH2CH2OCH3, CH2CH2CH2F, CH2CF3, 3,3,3-trifluoropropyl, 4,4,4-trifluorobutyl, or -(CH2)-R6; R6 is a C3-C6 cycloalkyl, 2-tetrahydrofurane, or 3-tetrahydrofurane; R7 is a C1-C3 alkyl, CF3, or N(R4)2, and pharmaceutically acceptable salts thereof are disclosed. Also pharmaceutical compositions comprising the above compounds and methods wherein the above compounds are used for treatment of disorders in the central nervous system are disclosed.

  式 1 的新取代 4-(苯基-N-烷基)-哌啶化合物： 其中 X 是 CH；R1 是 CF3、OSO2 、OSO2 、SOR7、SO2R7、COR7、CN、OR3、NO2、CONHR3、3-噻吩、2-噻吩、3-呋喃、2-呋喃、F、Cl、Br 或 I；R2 是 F、Cl、Br、I、CN、 、CH3、O 、OH 和 NH2；R3 和 R4 是 H；R5是C1-C4烷基、烯丙基、 S 、 O 、 F、 、3,3,3-三氟丙基、4,4,4-三氟丁基或-(CH2)-R6；R6是C3-C6环烷基、2-四氢呋喃或3-四氢呋喃；R7是C1-C3烷基、 或N(R4)2，以及其药学上可接受的盐。 此外，还公开了包含上述化合物的药物组合物，以及将上述化合物用于治疗中枢神经系统疾病的方法。
• Small molecule inhibitors of the nuclear translocation of androgen receptor for the treatment of castration-resistant prostate cancer
  申请人：University of Pittsburgh—Of the Commonwealth System of Higher Education

  公开号：US10980806B2

  公开（公告）日：2021-04-20

  A compound, or a pharmaceutically acceptable salt or ester thereof, according to formula I: R20—(Z)b—(Y)c—(R21)a—(X)d—R22—R23 wherein R20 is aryl, substituted aryl, heteroaryl, substituted heteroaryl, cycloalkyl, substituted cycloalkyl, heterocycloalkyl, substituted heterocycloalkyl, alkoxy, aryloxy, a thio-containing group, or a seleno-containing group; Z is alkanediyl, substituted alkanediyl, cycloalkanediyl, or substituted cycloalkanediyl; Y is S, O, S(═O), —S(═O)(═O)—, or NR10, wherein R10 is H or alkyl; R21 is alkanediyl, substituted alkanediyl, cycloalkanediyl, substituted cycloalkanediyl, alkadienyl, substituted alkadienyl, cycloalkenediyl, substituted cycloalkenediyl, alkatrienyl, substituted alkatrienyl; X is —C(═O)—, —S(═O)(═O)—, or —N(H)C(═O)—; R22 includes at least one divalent amino radical; R23 is aryl, substituted aryl, heteroaryl, substituted heteroaryl, cycloalkyl, substituted cycloalkyl, heterocycloalkyl, substituted heterocycloalkyl, alkoxy, aryloxy, a thio-containing group, or a seleno-containing group; a, b, c, and d independently are 0 or 1.

  一种符合式 I 的化合物或其药学上可接受的盐或酯： R20-(Z)b-(Y)c-(R21)a-(X)d-R22-R23 其中 R20 是芳基、取代的芳基、杂芳基、取代的杂芳基、环烷基、取代的环烷基、杂环烷基、取代的杂环烷基、烷氧基、芳氧基、含硫基的基团或含硒基的基团；Z 是烷二基、取代的烷二基、环烷二基或取代的环烷二基； Y 是 S、O、S(═O)、-S(═O)(═O)- 或 NR10，其中 R10 是 H 或烷基；R21是烷二基、取代的烷二基、环烷二基、取代的环烷二基、烷二烯基、取代的烷二烯基、环烷二基、取代的环烷二基、烷三烯基、取代的烷三烯基；X是-C(═O)-、-S(═O)(═O)-或-N(H)C(═O)-；R22 包括至少一个二价氨基； R23 是芳基、取代的芳基、杂芳基、取代的杂芳基、环烷基、取代的环烷基、杂环烷基、取代的杂环烷基、烷氧基、芳氧基、含硫醚基团或含硒基团；a、b、c 和 d 独立地为 0 或 1。
• Synthesis, Screening, and Molecular Modeling of New Potent and Selective Antagonists at the α_1d Adrenergic Receptor
  作者：Amedeo Leonardi、Daniela Barlocco、Federica Montesano、Giorgio Cignarella、Gianni Motta、Rodolfo Testa、Elena Poggesi、Michele Seeber、Pier G. De Benedetti、Francesca Fanelli

  DOI：10.1021/jm030944+

  日期：2004.4.1

  In the present study, more than 75 compounds structurally related to BMY 7378 have been designed and synthesized. Structural variations of each part of the reference molecule have been introduced, obtaining highly selective ligands for the aid adrenergic receptor. The molecular determinants for selectivity at this receptor are essentially, held by the phenyl substituent in the phenylpiperazine moiety. The integration of an extensive SAR analysis with docking simulations using the rhodopsin-based models of the three alpha(1)-AR subtypes and of the 5-HT1A receptor provides significant insights into the characterization of the receptor binding sites as well as into the molecular determinants of ligand selectivity at the alpha(1d)-AR and the 5-HT1A receptors. The results of multiple copies simultaneous search (MCSS) on the substituted phenylpiperazines together with those of manual docking of compounds BAN 7378 and 69 into the putative binding sites of the alpha(1a)-AR, alpha(1b)-AR, alpha(1d)-AR, and the 5-HT1A receptors suggest that the phenylpiperazine moiety would dock into a site formed by amino acids in helices 3, 4, 5, 6 and extracellular loop 2, (E2), whereas the spirocyclic ring of the ligand docks into a site formed by amino acids of helices 1, 2, 3, and 7. This docking mode is consistent with the SAR data produced in this work. Furthermore, the binding site of the imide moiety does not allow for the simultaneous involvement of the two carbonyl oxygen atoms in H-bonding, interactions, consistent with the SAR data, in particular with the results obtained with the lactam derivative 128. The results of docking simulations also suggest that the second and third extracellular loops may act as selectivity filters for the substituted phenylpiperazines. The most potent and selective compounds for alpha(1d) adrenergic receptor, i.e., 69 (Rec 26D/038) and 128 (Rec 26D/073), are characterized by the presence of the 2,5-dichlorophenylpiperazine moiety.