4,4-Diphenyl-1-butyliodide | 169756-94-9

• 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-Diphenyl-1-butyliodide
• 英文别名: 4,4-diphenyl-1-iodobutane；1,1-diphenyl-4-iodobutane；4,4-diphenylbutyl iodide；(4-iodo-1-phenylbutyl)benzene
• CAS: 169756-94-9
• 化学式: C₁₆H₁₇I
• 分子量: 336.215
• InChiKey: QAHACWQRIKXIJN-UHFFFAOYSA-N

物化性质

• 沸点：
  377.8±31.0 °C(Predicted)
• 密度：
  1.413±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  4,4-Diphenyl-1-butyliodide 在 palladium on activated charcoal sodium azide 、 氢气 、 溶剂黄146 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 4,4-二(苯基)丁烷-1-胺
  参考文献：
  名称：

  Selective inhibitors of GABA uptake: synthesis and molecular pharmacology of 4-N-methylamino-4,5,6,7-tetrahydrobenzo[d]isoxazol-3-ol analogues

  摘要：

  A series of lipophilic diaromatic derivatives of the glia-selective GABA uptake inhibitor (R)-4-amino-4,5,6,7-tetrahydrobenzo[d]isoxazol-3-ol [(R)-exo-THPO, 4] were synthesized via reductive amination of 3-ethoxy-4,5,6,7-tetrahydrobenzo[d]isoxazol-4-one (9) or via N-alkylation of O-alkylatedracemic 4. The effects of the target compounds on GABA uptake mechanisms in vitro were measured using a rat brain synaptosomal preparation or primary cultures of mouse cortical neurons and glia cells (astrocytes), as well as HEK cells transfected with cloned mouse GABA transporter subtypes (GAT1-4). The activity against isoniazid-induced convulsions in mice after subcutaneous administration of the compounds was determined. All of the compounds were potent inhibitors of synaptosomal uptake the most potent compound being (RS)-4-[N-(1,1-diphenylbut-1-4-en-yl)amino]-4,5,6,7-tetrahydrobenzo[d]isoxazol-3-ol (17a, IC50 = 0.14 muM). The majority of the compounds showed a weak preference for glial, as compared to neuronal, GABA uptake. The highest degree of selectivity was 10-fold corresponding to the glia selectivity of (R)-N-methyl-exo-THPO (5). All derivatives showed a preference for the GAT1 transporter, as compared with GAT2-4, with the exception of (RS)-4-[N-[1,1-bis(3-methyl-2-thienyl)but-1-en-4-yl]-N-methylamino]-4,5,6,7-tetrahydrobenzo[d]isoxazol-3-ol (28d), which quite surprisingly turned out to be more potent than GABA at both GAT1 and GAT2 subtypes. The GAT1 activity was shown to reside in (R)-28d whereas (R)-28d and (S)-28d contributed equally to GAT2 activity. This makes (S)-28d a GAT2 selective compound, and (R)-28d equally effective in inhibition of GAT1 and GAT2 mediated GABA transport. All compounds tested were effective as anticonvulsant reflecting that these compounds have blood-brain barrier permeating ability. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.10.029
• 作为产物：
  描述：

  (4-碘-1-苯基丁-1-烯基)苯 在 碘 、 环庚酮 作用下， 以 正己烷 为溶剂， 以64%的产率得到4,4-Diphenyl-1-butyliodide
  参考文献：
  名称：

  碘促进二氢从酮到烯烃、三苯甲基和二苯甲基衍生物的转移

  摘要：

  在此，一类新型转移氢化剂环庚酮被成功用于碘促进的无金属氢化。一系列烯烃、三苯甲基衍生物和二苯甲基衍生物被还原为所需化合物，产率中等至优异。使用α-氘代环十二酮进行烯烃的转移加氢氘化表现出高区域选择性。初步的机理研究证实了参与烯烃还原的两个氢原子的起源。目前的研究为在化学合成中使用酮作为独特的转移氢化剂铺平了道路。

  DOI：

  10.1039/d3cc03409g

文献信息

• Tricyclic compounds, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US06248766B1

  公开（公告）日：2001-06-19

  A compound of the formula: wherein R1 is H or a substituent; m is 1-3; Ar is an aromatic group which may be substituted; X is a bond or a divalent straight-chain group having 1-6 atoms which may be substituted; Y is —S—, —O—, or —N(R2— (R2 is H or a substituent group), Z is —N═ or —C(R3)═ (R3 is H or a hydrocarbon group), ring A is a benzene ring; ring B is a 5- to 7-membered ring which may be substituted, or a salt thereof is useful for eliciting a prostaglandin I2 receptor agonistic effect.

  该公式的化合物： 其中R1为H或取代基；m为1-3；Ar为可能被取代的芳香基团；X为键或具有1-6个原子的二价直链基团，可能被取代；Y为—S—，—O—或—N(R2— (R2为H或取代基团)，Z为—N═或—C(R3)═ (R3为H或碳氢基团)，环A为苯环；环B为可能被取代的5-至7-成员环，或其盐对诱导前列腺素I2受体激动效应有用。
• 4-aminotetrahydrobenzisoxazole or -isothiazole compounds
  申请人：H. Lundbeck A/S

  公开号：US05998613A1

  公开（公告）日：1999-12-07

  The present invention relates to novel 4-aminotetrahydrobenzisoxazoles or 4-aminotetrahydrobenziothiazoles having gamma-aminobutanoic acid (GABA)-uptake inhibiting activity and thus useful in the treatment of analgesia, psychosis, convulsions, anxiety, epileptic disorders or muscular and movement disorders, such as spastic disorders or symptoms in Huntington's disease or Parkinson disease.

  本发明涉及具有γ-氨基丁酸（GABA）摄取抑制活性的新型4-氨基四氢苯并异噁唑或4-氨基四氢苯并噻唑，因此在治疗疼痛、精神病、抽搐、焦虑、癫痫性疾病或肌肉和运动障碍方面具有用处，如在亨廷顿病或帕金森病中的痉挛障碍或症状。
• Pharmaceutical compounds
  申请人：Eli Lilly and Company

  公开号：US05589501A1

  公开（公告）日：1996-12-31

  A pharmaceutical compound of the formula ##STR1## in which m is 0, 1 or 2, n and q are each 0 or 1 to 5, and p is 0 or 1, X is --CO.sub.2 H or tetrazolyl, Y is --CH.dbd.CH--, and Z is (i) phenyl, naphthyl or thienyl, said phenyl, naphthyl and thienyl being optionally substituted, (ii) --CHR.sup.1 R.sup.2 where R.sup.1 and R.sup.2 are each phenyl, naphthyl or thienyl, said phenyl, naphthyl and thienyl being optionally substituted, (iii) .dbd.CR.sup.1 R.sup.2 where R.sup.1 and R.sup.2 are each phenyl, naphthyl or thienyl, said phenyl, naphthyl and thienyl being optionally substituted, or (iv) ##STR2## where r is 0 or 1 to 3 and the phenyl rings are optionally substituted; provided that when Z is phenyl and m is 1, p is 1; and salts and esters thereof.

  一种药物化合物的化学式为##STR1##其中m为0、1或2，n和q各自为0或1至5，p为0或1，X为--CO.sub.2 H或四唑基，Y为--CH.dbd.CH--，Z为(i)苯基、萘基或噻吩基，所述苯基、萘基和噻吩基可选地被取代，(ii)--CHR.sup.1 R.sup.2，其中R.sup.1和R.sup.2各自为苯基、萘基或噻吩基，所述苯基、萘基和噻吩基可选地被取代，(iii).dbd.CR.sup.1 R.sup.2，其中R.sup.1和R.sup.2各自为苯基、萘基或噻吩基，所述苯基、萘基和噻吩基可选地被取代，或(iv)##STR2##其中r为0或1至3，苯环可选地被取代；但当Z为苯基且m为1时，p为1；以及其盐和酯。
• [EN] 4-AMINOTETRAHYDROBENZISOXAZOLE OR -ISOTHIAZOLE COMPOUNDS<br/>[FR] COMPOSES 4-AMINOTETRAHYDROBENZISOXAZOLE OU -ISOTHIAZOLE
  申请人：H. LUNDBECK A/S

  公开号：WO1996026929A1

  公开（公告）日：1996-09-06

  (EN) 4-aminotetrahydrobenzisoxazole or -isothiazole compounds having general formulae (Ia) and (Ib), wherein R1-R6, X and P are further defined in the description. The disclosed compounds have GABA (4-aminobutanoic acid) inhibiting activity and are useful in the treatment of analgesia, psychosis, convulsions, anxiety or muscular and movement disorders, especially epilepsy.(FR) Cette invention concerne des composés 4-aminotétrahydrobenzisoxazole ou -isothiazole représentés par les formules générales (Ia) et (Ib) dans lesquelles R1-R6, X et P sont définis par ailleurs dans le descriptif de l'invention. Ces composés présentent une activité inhibante vis-à-vis du GABA (acide 4-aminobutanoïque) et s'avèrent utiles pour le traitement de l'analgésie, de la psychose, des convulsions, de l'anxiété ou des troubles musculaires et des dyskinésies, et tout particulièrement de l'épilepsie.

  (中文) 公开的化合物为具有一般式（Ia）和（Ib）的4-氨基四氢苯并异噁唑或异噻唑化合物，其中R1-R6，X和P在描述中有进一步定义。这些化合物具有GABA（4-氨基丁酸）抑制活性，可用于治疗疼痛、精神病、抽搐、焦虑或肌肉和运动障碍，特别是癫痫。
• [EN] EXCITATORY AMINO ACID RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DES RECEPTEURS D'ACIDES AMINES EXCITATEURS
  申请人：ELI LILLY AND COMPANY

  公开号：WO1996007405A1

  公开（公告）日：1996-03-14

  (EN) The present invention provides compounds of formula (I) in which R is as defined in the specification, or a pharmaceutically acceptable metabolically labile ester or amide thereof, or a pharmaceutically acceptable salt thereof, which are useful as antagonists of one or more of the actions of L-glutamate at metabotropic excitatory amino acid receptors.(FR) Cette invention concerne des composés de formule (I), dans laquelle R est tel que défini dans le descriptif, ou un ester ou amide pharmaceutiquement acceptable de ces composés qui est métaboliquement labile, ou encore un sel pharmaceutiquement acceptable de ces composés, qu'on utilise comme antagonistes d'une ou de plusieurs actions du L-glutamate au niveau des récepteurs d'acides aminés excitateurs métabotropiques.

  本发明提供了公式（I）的化合物，其中R如规范中定义，或其药物可接受的代谢易裂解酯或酰胺，或其药物可接受的盐，这些化合物是L-谷氨酸在代谢型兴奋性氨基酸受体上的一个或多个作用的拮抗剂。