DHP-359 | 4684-13-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: DHP-359
• 英文别名: DPH-359；N.N-Dimethyl-fluoren-Δ^9.γ-propylamin；9-<3-Dimethylamino-propyliden>-fluoren；9-(3-Dimethylaminopropyliden)fluoren；9-(3-Dimethylamino-propyliden)-fluoren；3-(9H-Fluoren-9-ylidene)-N,N-dimethyl-1-propanamine；3-fluoren-9-ylidene-N,N-dimethylpropan-1-amine
• CAS: 4684-13-3
• 化学式: C₁₈H₁₉N
• 分子量: 249.356
• InChiKey: VEZSADRTEPJSMU-UHFFFAOYSA-N

物化性质

• 沸点：
  379.0±21.0 °C(Predicted)
• 密度：
  1.121±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 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：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  DHP-359 生成 9-allylidene-9H-fluorene
  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 DHP-359
  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

• [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.