(4,4-二苯基-丁-3-烯基)-二甲基-胺 | 46970-87-0

• 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: (4,4-二苯基-丁-3-烯基)-二甲基-胺
• 英文名称: N,N-dimethyl-4,4-diphenyl-3-butenylamine
• 英文别名: 1,1-Diphenyl-4-dimethylamino-buten-(1)；4-Dimethylamino-1,1-diphenyl-buten-(1)；Dimethyl-(4,4-diphenyl-but-3-enyl)-amin；DHP-362；(4,4-diphenyl-but-3-enyl)-dimethyl-amine；DPH-362；N,N-dimethyl-4,4-diphenylbut-3-en-1-amine
• CAS: 46970-87-0
• 化学式: C₁₈H₂₁N
• 分子量: 251.371
• InChiKey: ZRPJJBLGKLVADE-UHFFFAOYSA-N

物化性质

• 沸点：
  381.5±42.0 °C(Predicted)
• 密度：
  0.991±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4,4-二苯基-丁-3-烯基)-二甲基-胺 生成 1,1-二苯基-1,3-丁二烯
  参考文献：
  名称：

  Holm,T., Acta Chemica Scandinavica (1947), 1963, vol. 17, p. 2437 - 2443

  摘要：

  DOI：
• 作为产物：
  描述：

  N,N-二甲基-3-氯丙胺 在 盐酸 、 碘 、 magnesium 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 (4,4-二苯基-丁-3-烯基)-二甲基-胺
  参考文献：
  名称：

  Discovery of diphenyl amine based sodium channel blockers, effective against hNav1.2

  摘要：

  The development of new therapies for chronic pain is an area of unmet medical need. Central to pathways of chronic pain is the upregulation of voltage-gated sodium channels. The use of tricyclic antidepressants, which also have sodium channel activity, in chronic pain therapy prompted us to develop novel compounds from this scaffold. Herein, we show that the tricyclic moiety is not needed for effective inhibition of the [H-3]-BTX binding site and sodium currents of hNa(v)1.2. Our lead compound 6, containing a diphenyl amine motif, demonstrated a 53% inhibitory block of Na(v)1.2 currents at 10 mu M, which is greater than 50% increase in current block in comparison to the amitriptyline standard. Altogether our study establishes that the tricyclic motif is unnecessary for hNa(v)1.2 activity and modification of the amine portion is detrimental to sodium channel block. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.010

文献信息

• Synthesis of Novel Quaternary Ammonium Salts and Their in Vitro Antileishmanial Activity and U-937 Cell Cytotoxicity
  作者：Sandra Duque-Benítez、Luz Ríos-Vásquez、Rogelio Ocampo-Cardona、David Cedeño、Marjorie Jones、Iván Vélez、Sara Robledo

  DOI：10.3390/molecules21040381

  日期：——

  halomethylated choline analogs (series III). Assessments of their in vitro cytotoxicity in human promonocytic cells U-937 and antileishmanial activity in axenic amastigotes of L. (Viannia) panamensis (M/HOM/87/UA140-pIR-eGFP) were carried out using the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-tetrazolium bromide) micromethod. Antileishmanial activity was also tested in intracellular amastigotes of L. (V) panamensis

  这项工作描述了一系列季铵盐的合成以及它们的体外抗菌活性和细胞毒性的评估。还包括对化合物的结构-活性关系的初步讨论。制备了三个系列的季铵盐：（i）卤甲基化的季铵盐（系列I）；（ii）非卤化季铵盐（II系列）和（iii）卤甲基化胆碱类似物（III系列）。使用MTT（3-（4 （5-5-二甲基噻唑-2-基）-2，5-二苯基-溴化四唑）微方法。还对L.的胞内变形虫测试了抗利什曼活性。（五）巴拿马流式细胞仪。大多数化合物对人U937细胞具有高毒性，其致命浓度50（LC50）值在9至46μg/ mL范围内。大多数化合物证明具有抗菌活性。在轴突性吻合动物中，抗菌活性从14到57μg/ mL不等，而在细胞内的吻合动物中，其活性从17到50μg/ mL不等。N-氯甲基-N，N-二甲基-N-（4,4-二苯基丁-3-烯-1-基）碘化铵（1a），N-碘甲基-N，N-二甲基-N-（4,4-二苯基丁-3-烯-1-基）
• [EN] NOVEL TRICYCLIC, BICYCLIC, MONOCYCLIC, AND ACYCLIC AMINES AS POTENT SODIUM CHANNEL BLOCKING AGENTS<br/>[FR] NOUVEAUX AMINES TRICYCLIQUES, BICYCLIQUES, MONOCYCLIQUES ET ACYCLIQUES UTILES COMME AGENTS BLOQUANTS PUISSANTS DES CANAUX DE SODIUM
  申请人：UNIV VIRGINIA

  公开号：WO2006023757A3

  公开（公告）日：2006-08-03
• Holm,T., Acta Chemica Scandinavica (1947), 1963, vol. 17, p. 2437 - 2443
  作者：Holm,T.

  DOI：——

  日期：——
• Discovery of diphenyl amine based sodium channel blockers, effective against hNav1.2
  作者：Debjani P. Hudgens、Catherine Taylor、Timothy W. Batts、Manoj K. Patel、Milton L. Brown

  DOI：10.1016/j.bmc.2006.09.010

  日期：2006.12

  The development of new therapies for chronic pain is an area of unmet medical need. Central to pathways of chronic pain is the upregulation of voltage-gated sodium channels. The use of tricyclic antidepressants, which also have sodium channel activity, in chronic pain therapy prompted us to develop novel compounds from this scaffold. Herein, we show that the tricyclic moiety is not needed for effective inhibition of the [H-3]-BTX binding site and sodium currents of hNa(v)1.2. Our lead compound 6, containing a diphenyl amine motif, demonstrated a 53% inhibitory block of Na(v)1.2 currents at 10 mu M, which is greater than 50% increase in current block in comparison to the amitriptyline standard. Altogether our study establishes that the tricyclic motif is unnecessary for hNa(v)1.2 activity and modification of the amine portion is detrimental to sodium channel block. (c) 2006 Elsevier Ltd. All rights reserved.