4-[4-(4-fluorobenzyl)phenyl]-1,2,3,6-tetrahydropyridine | 181207-58-9

• 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-(4-fluorobenzyl)phenyl]-1,2,3,6-tetrahydropyridine
• 英文别名: 4-[4-(4-fluorophenyl)methylphenyl]-1,2,3,6-tetrahydropyridine；4-[4-[(4-Fluorophenyl)methyl]phenyl]-1,2,3,6-tetrahydropyridine
• CAS: 181207-58-9
• 化学式: C₁₈H₁₈FN
• 分子量: 267.346
• InChiKey: IPBBAQYVEKEDOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[4-(4-fluorobenzyl)phenyl]-1,2,3,6-tetrahydropyridine 生成 4-[4-(4-fluorobenzyl)phenyl]piperidine
  参考文献：
  名称：

  Arylpiperidine and arylpiperazine derivatives and medicament containing

  摘要：

  该化合物的化学式（I）或其盐或含有相同化合物的药物##STR1##其中，A和B代表羰基或磺酰基，m和p不同，分别代表0或1，R.sup.1和R.sup.2可以相同也可以不同，分别代表氢原子，未取代或取代的烷基，未取代或取代的芳基，未取代或取代的芳基烷基，含氮的未取代或取代的杂环基或含氧的未取代或取代的杂环基，或者R.sup.1和R.sup.2连同它们连接的氮原子，可以形成未取代或取代的杂环基，但是当B是磺酰基时，R.sup.2不代表氢原子，n是1到6的整数，X代表亚甲基或氧原子，E和Y可以相同也可以不同，分别代表氢原子，卤素原子，烷氧基，或者可以被卤素原子取代的烷基，点线表示键的存在或不存在，当点线表示键存在时，Z代表碳原子，当点线表示键不存在时，Z代表CH或氮原子。

  公开号：

  US05723475A1
• 作为产物：
  描述：

  4-bromo-4'-fluorodiphenylmethanol 在 三乙基硅烷 、 正丁基锂 、 三氟乙酸 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 、 三氟乙酸 为溶剂， 反应 3.0h， 生成 4-[4-(4-fluorobenzyl)phenyl]-1,2,3,6-tetrahydropyridine
  参考文献：
  名称：

  Synthesis and biological evaluation of new 4-arylpiperidines and 4-aryl-4-piperidinols: dual Na+ and Ca2+ channel blockers with reduced affinity for dopamine D2 receptors

  摘要：

  A series of novel 4-arylpiperidines and 4-aryl-4-piperidinols (2a-f, 3a f and 4a-f) wits synthesized and evaluated for blocking effects on both neuronal Na+ and T-type Ca2+ channels and binding affinity for dopamine D-2 receptors. Most or the compounds blockaded both ion channels with potency greater than or equal to flunarizine Ia which was adopted as a reference standard. In addition, these compounds had significantly reduced affinity for dopamine D-2 receptors which is common in this class of structure. Compounds 2a-f, 3a-f and 4a-f exhibited potent anticonvulsant effects following systemic (ip) administration on audiogenic seizures in DBA/2 mice, indicating their excellent brain permeability. The neuroprotective activity of 2a, 3a and 4a was also assessed in a transient middle cerebral artery Occlusion (MCAO) model. These Compounds significantly reduced neuronal damage without affecting ischemic hyperthemia, while flunarizine Ia produced only minor reductions. In particular. 4a had 1.7-fold the potency in this MCAO model but only 1/20 the affinity for dopamine D-2 receptors of 1a. The Superposition of 2a, 3a and 4a on the basis of analyses of systematic conformation and similar structure has revealed that the cinnamyl, phenacyl and phenoxy-propanol groups are likely to be structurally and biologically equivalent. Moreover, the Superposition of 2a and 2f shows that diphenyl ether and biphenyl groups occupy a similar space, suggesting that both groups act as a bioisostere for the blockade of ion channels: however, this is not the case for dopamine D-2 receptors since only biphenyl Compounds such as 2f had high affinity similar to flunarizine Ia. Compound 4a (SUN N5030) has a good pharmacological profile and may be Useful in the alleviation and treatment or ischemic diseases. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00288-7

文献信息

• Arylpiperidine and arylpiperazine derivatives and medicament containing
  申请人：Suntory Limited

  公开号：US05723475A1

  公开（公告）日：1998-03-03

  The compound of the formula (I) or its salt or a medicament containing the same ##STR1## wherein, A and B represent a carbonyl group or sulfonyl group, m and p are different and represent 0 or 1, R.sup.1 and R.sup.2 may be the same or different from each other and represent a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted heterocyclic group containing nitrogen or an unsubstituted or substituted heterocyclic group containing oxygen, or R.sup.1 and R.sup.2, taken together with the nitrogen atom to which they are linked, may form an unsubstituted or substituted heterocyclic group, provided that when B is a sulfonyl group, R.sup.2 does not represent a hydrogen atom, n is an integer of 1 to 6, X represents a methylene group or an oxygen atom, E and Y may be the same or different from each other and represent a hydrogen atom, a halogen atom, an alkoxy group, or an alkyl group which may be substituted by a halogen atom the dotted line shows the presence or absence of a bond, when said dotted line shows the presence of a bond, Z represents a carbon atom, and when said dotted line shows the absence of a bond, Z represents CH or a nitrogen atom.

  该化合物的化学式（I）或其盐或含有相同化合物的药物##STR1##其中，A和B代表羰基或磺酰基，m和p不同，分别代表0或1，R.sup.1和R.sup.2可以相同也可以不同，分别代表氢原子，未取代或取代的烷基，未取代或取代的芳基，未取代或取代的芳基烷基，含氮的未取代或取代的杂环基或含氧的未取代或取代的杂环基，或者R.sup.1和R.sup.2连同它们连接的氮原子，可以形成未取代或取代的杂环基，但是当B是磺酰基时，R.sup.2不代表氢原子，n是1到6的整数，X代表亚甲基或氧原子，E和Y可以相同也可以不同，分别代表氢原子，卤素原子，烷氧基，或者可以被卤素原子取代的烷基，点线表示键的存在或不存在，当点线表示键存在时，Z代表碳原子，当点线表示键不存在时，Z代表CH或氮原子。
• Arylipiperdinopropanol and arylipiperazinopropanol derivatives and pharmaceuticals containing the same
  申请人：Annoura Hirokazu

  公开号：US20050101610A1

  公开（公告）日：2005-05-12

  A compound having the formula (I) or its salt, hydrate, hydrate salt or solvate: wherein R 1 to R 4 independently represent H, halogen, OH, alkoxy, optionally substituted alkyl, aryl, or aralkyl group, R 5 represents H, optionally substituted alkyl, aryl, or aralkyl group, E 1 represents O, S, or —NR 6 , where R 6 represents H, an optionally substituted alkyl, aryl, or aralkyl group, E 2 represents O, S, or —NR 7 , where R 7 represents H, an optionally substituted alkyl, aryl, or aralkyl group, A represents CH, C(OH), or N, X represents H, halogen, alkoxy, or an optionally substituted alkyl group, and Q represents an optionally substituted phenyl group, phenoxy, phenylmethyl, or cycloalkyloxy group, where when E 1 represents O or S, E 2 does not represent O or S, which has an action of suppressing the cytotoxic Ca 2+ overload and lipid peroxidation and effective for pharmaceutical preparation for the alleviation and treatment of symptoms due to ischemic diseases, etc.

  化合物具有以下公式(I)或其盐，水合物，水合盐或溶剂化物： 其中，R1至R4独立地表示H，卤素，OH，烷氧基，可选择取代的烷基，芳基或芳基烷基，R5表示H，可选择取代的烷基，芳基或芳基烷基，E1表示O，S或-NR6，其中R6表示H，可选择取代的烷基，芳基或芳基烷基，E2表示O，S或-NR7，其中R7表示H，可选择取代的烷基，芳基或芳基烷基，A表示CH，C（OH）或N，X表示H，卤素，烷氧基或可选择取代的烷基，Q表示可选择取代的苯基，苯氧基，苯甲基或环烷氧基，其中当E1表示O或S时，E2不表示O或S，该化合物具有抑制细胞毒性Ca2+过载和脂质过氧化作用，并且对于缓解和治疗缺血性疾病症状等方面的制药制剂具有有效作用。
• Arylpiperidinopropanol and arylpiperazinopropanol derivatives and pharmaceuticals containing the same
  申请人：——

  公开号：US20030236269A1

  公开（公告）日：2003-12-25

  A compound having the formula (I) or its salt, hydrate, hydrate salt or solvate: 1 wherein R 1 to R 4 independently represent H, halogen, OH, alkoxy, optionally substituted alkyl, aryl, or aralkyl group, R 5 represents H, optionally substituted alkyl, aryl, or aralkyl group, E 1 represents O, S, or —NR 6 , where R 6 represents H, an optionally substituted alkyl, aryl, or aralkyl group, E 2 represents O, S, or —NR 7 , where R 7 represents H, an optionally substituted alkyl, aryl, or aralkyl group, A represents CH, C(OH), or N, X represents H, halogen, alkoxy, or an optionally substituted alkyl group, and Q represents an optionally substituted phenyl group, phenoxy, phenylmethyl, or cycloalkyloxy group, where when E 1 represents O or S, E 2 does not represent O or S, which has an action of suppressing the cytotoxic Ca 2+ overload and lipid peroxidation and effective for pharmaceutical preparation for the alleviation and treatment of symptoms due to ischemic diseases, etc.

  化合物具有公式(I)或其盐、水合物、水合盐或溶剂化物：其中R1至R4独立地表示H、卤素、OH、烷氧基、可选地取代的烷基、芳基或芳基烷基，R5表示H、可选地取代的烷基、芳基或芳基烷基，E1表示O、S或-NR6，其中R6表示H、可选地取代的烷基、芳基或芳基烷基，E2表示O、S或-NR7，其中R7表示H、可选地取代的烷基、芳基或芳基烷基，A表示CH、C（OH）或N，X表示H、卤素、烷氧基或可选地取代的烷基基团，Q表示可选地取代的苯基、苯氧基、苯甲基或环烷氧基基团，当E1表示O或S时，E2不表示O或S，该化合物具有抑制细胞毒性Ca2+过载和脂质过氧化作用，对于缓解和治疗缺血性疾病症状等方面的制药制剂具有有效作用。
• AMELIORANT OR REMEDY FOR SYMPTOMS CAUSED BY ISCHEMIC DISEASES AND COMPOUNDS USEFUL THEREFOR
  申请人：SUNTORY LIMITED

  公开号：EP0755923A1

  公开（公告）日：1997-01-29

  A medicine having the following basic structure, for the alleviation or treatment of symptoms derived from ischemic diseases and seizures, epilepsy, and migraine, having a powerful action in suppressing cytotoxic Ca2+ overload and free from side-effects: wherein Z = C, CH, or N, X = O or CH2, E and Y = H, OH, a halogen, alkoxy, alkyl, or a halogen-substituted alkyl.

  一种具有以下基本结构的药物，用于缓解或治疗缺血性疾病和癫痫发作、癫痫和偏头痛引起的症状，在抑制细胞毒性 Ca2+ 过载方面具有强大的作用，且无副作用： 其中 Z = C、CH 或 N，X = O 或 CH2，E 和 Y = H、OH、卤素、烷氧基、烷基或卤素取代的烷基。
• ARYLPIPERIDINE AND ARYLPIPERAZINE DERIVATIVES AND DRUGS CONTAINING THE SAME
  申请人：SUNTORY LIMITED

  公开号：EP0757986A1

  公开（公告）日：1997-02-12

  The compound of the formula (I) or its salt or a medicament containing the same wherein, A and B represent a carbonyl group or sulfonyl group, m and p are different and represent 0 or 1, R1 and R2 may be the same or different from each other and represent a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted heterocyclic group containing nitrogen or an unsubstituted or substituted heterocyclic group containing oxygen, or R1 and R2, taken together with the nitrogen atom to which they are linked, may form an unsubstituted or substituted heterocyclic group, provided that when B is a sulfonyl group, R2 does not represent a hydrogen atom, n is an integer of 1 to 6, X represents a methylene group or an oxygen atom, E and Y may be the same or different from each other and represent a hydrogen atom, a halogen atom, an alkoxy group, or an alkyl group which may be substituted by a halogen atom    the dotted line shows the presence or absence of a bond,    when said dotted line shows the presence of a bond, Z represents a carbon atom, and when said dotted line shows the absence of a bond, Z represents CH or a nitrogen atom.

  式 (I) 的化合物或其盐或含有相同成分的药物 其中 A 和 B 代表羰基或磺酰基、 m 和 p 不同，代表 0 或 1、 R1 和 R2 可以相同或不同，代表氢原子、未取代或取代的烷基、未取代或取代的芳基、未取代或取代的芳烷基、未取代或取代的含氮杂环基团，或未取代或取代的含氧杂环基团，或 R1 和 R2 连同与其相连的氮原子可组成未取代或取代的杂环基团，但当 B 为磺酰基时，R2 不代表氢原子、 n 是 1 至 6 的整数、 X 代表亚甲基或氧原子、 E 和 Y 可以相同，也可以不同，代表氢原子、卤素原子、烷氧基或可被卤素原子取代的烷基 虚线表示键的存在或不存在、 当所述虚线表示存在键时，Z 代表碳原子；当所述虚线表示不存在键时，Z 代表 CH 或氮原子。