1-{4-[(5-Bromo-pyridin-2-yl)-(3,4-dichloro-benzyl)-amino]-butyl}-3-[3-(1-trityl-1H-imidazol-4-yl)-propyl]-thiourea | 218957-65-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-{4-[(5-Bromo-pyridin-2-yl)-(3,4-dichloro-benzyl)-amino]-butyl}-3-[3-(1-trityl-1H-imidazol-4-yl)-propyl]-thiourea
• CAS: 218957-65-4
• 化学式: C₄₂H₄₁BrCl₂N₆S
• 分子量: 812.704
• InChiKey: RXANJCVYQNSMEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.07
• 重原子数：
  52.0
• 可旋转键数：
  16.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  58.01
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-{4-[(5-Bromo-pyridin-2-yl)-(3,4-dichloro-benzyl)-amino]-butyl}-3-[3-(1-trityl-1H-imidazol-4-yl)-propyl]-thiourea 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以18%的产率得到1-(4-(N-(5-Bromopyridin-2-yl)-N-(3,4-dichlorobenzyl)amino)butyl)-3-(3-(1H-imidazol-4-yl)propyl)thiourea
  参考文献：
  名称：

  Nonpeptide Somatostatin Agonists with sst₄ Selectivity:  Synthesis and Structure−Activity Relationships of Thioureas

  摘要：

  Utilizing NNC 26-9100 (11) as a structural lead, a variety of nonpeptide derivatives of somatostatin were synthesized and evaluated for sst(2) and sst(4) receptor binding affinity. A novel thiourea scaffold was utilized to attach (1) a heteroaromatic nucleus to mimic the Trp(8) residue, (2) a nonheteroaromatic nucleus to mimic Phe(7), and (3) a primary amine or other basic group to mimic the Lys(9) residue of somatostatin. Displacement studies were carried out using membranes from cell lines expressing ssts [BHK cells (sst(4)) and HEK 293 cells (sst(2))] utilizing [I-125]Tyr(11)-SRIF as the radioligand. Several thioureas (11, 38, 39, 41, and 42) and the urea 66 exhibited K-i values of less than 100 nM. The thioureas 11 (K-i = 6 nM) and 41 (K-i = 16 nM) and the urea 66 (K-i = 14 nM) are believed to be the most potent nonpeptide sst(4) agonists known. Since the thiourea 11 and the urea 66 exhibit high ssts selectivity, these novel nonpeptide derivatives may be useful tools for studying the sst(4) receptor. Studies are currently in progress to evaluate the therapeutic potential of NNC 26-9100 (11) in the treatment of glaucoma.

  DOI：

  10.1021/jm980118e
• 作为产物：
  描述：

  2,5-二溴吡啶 在 吡啶 、 sodium hydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 1-{4-[(5-Bromo-pyridin-2-yl)-(3,4-dichloro-benzyl)-amino]-butyl}-3-[3-(1-trityl-1H-imidazol-4-yl)-propyl]-thiourea
  参考文献：
  名称：

  Nonpeptide Somatostatin Agonists with sst₄ Selectivity:  Synthesis and Structure−Activity Relationships of Thioureas

  摘要：

  Utilizing NNC 26-9100 (11) as a structural lead, a variety of nonpeptide derivatives of somatostatin were synthesized and evaluated for sst(2) and sst(4) receptor binding affinity. A novel thiourea scaffold was utilized to attach (1) a heteroaromatic nucleus to mimic the Trp(8) residue, (2) a nonheteroaromatic nucleus to mimic Phe(7), and (3) a primary amine or other basic group to mimic the Lys(9) residue of somatostatin. Displacement studies were carried out using membranes from cell lines expressing ssts [BHK cells (sst(4)) and HEK 293 cells (sst(2))] utilizing [I-125]Tyr(11)-SRIF as the radioligand. Several thioureas (11, 38, 39, 41, and 42) and the urea 66 exhibited K-i values of less than 100 nM. The thioureas 11 (K-i = 6 nM) and 41 (K-i = 16 nM) and the urea 66 (K-i = 14 nM) are believed to be the most potent nonpeptide sst(4) agonists known. Since the thiourea 11 and the urea 66 exhibit high ssts selectivity, these novel nonpeptide derivatives may be useful tools for studying the sst(4) receptor. Studies are currently in progress to evaluate the therapeutic potential of NNC 26-9100 (11) in the treatment of glaucoma.

  DOI：

  10.1021/jm980118e