5-pentyl isothiocyanate | 199522-83-3

• 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: 5-pentyl isothiocyanate
• 英文别名: 5-[N-(5-bromopyrid-2-yl)-N-(3,4-dichlorobenzyl)]aminopentyl isothiocyanate；5-bromo-N-[(3,4-dichlorophenyl)methyl]-N-(5-isothiocyanatopentyl)pyridin-2-amine
• CAS: 199522-83-3
• 化学式: C₁₈H₁₈BrCl₂N₃S
• 分子量: 459.237
• InChiKey: LTOVWHLOOQUCGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  60.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-pentyl isothiocyanate 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 25.5h， 生成 1-(5-(N-(5-Bromopyridin-2-yl)-N-(3,4-dichlorobenzyl)amino)-pentyl)-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-N-(5-氨基戊基)-氨基-5-溴吡啶 在 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 2.0h， 生成 5-pentyl isothiocyanate
  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

文献信息

• USE OF SOMATOSTATIN AGONISTS AND ANTAGONISTS FOR TREATING DISEASES RELATED TO THE EYE
  申请人：NOVO NORDISK A/S

  公开号：EP1019050B1

  公开（公告）日：2002-03-20
• SOMATOSTATIN AGONISTS AND ANTAGONISTS
  申请人：NOVO NORDISK A/S

  公开号：EP0912551A1

  公开（公告）日：1999-05-06
• US6127343A
  申请人：——

  公开号：US6127343A

  公开（公告）日：2000-10-03
• US6159941A
  申请人：——

  公开号：US6159941A

  公开（公告）日：2000-12-12
• [EN] SOMATOSTATIN AGONISTS AND ANTAGONISTS<br/>[FR] AGONISTES ET ANTAGONISTES DE LA SOMATOSTATINE
  申请人：NOVO NORDISK A/S

  公开号：WO1997043278A1

  公开（公告）日：1997-11-20

  (EN) The present invention relates to somatostatin ligands (Ia) or (Ib) which are useful for treating medical disorders related to binding to human somatostatin receptor subtypes, wherein X is =S, =O, =NH, =NCOPh or =N(CN), A is aryl optionally substituted with halogen, amino, hydroxy, nitro, C1-6-alkyl, C1-6-alkoxy or aryl, B is aryl optionally substituted with halogen, amino, hydroxy, C1-6-alkyl, C1-6-alkoxy or aryl, D is aryl, amino, optionally substituted with halogen, amino, hydroxy, C1-6-alkyl, C1-6-alkoxy or aryl, or a pharmaceutically acceptable salt thereof.(FR) L'invention porte sur les ligands (Ia) et (Ib) de la somatostatine servant au traitement de troubles médicaux liés aux sous-types de récepteurs humains de la somatostatine, de formules ci-jointes dans lesquelles: X est =S, =O, =NH, =NCOPh ou =N(CN); A est aryle facultativement substitué par halogène, amino, hydroxy, nitro, C1-6-alkyle, C1-6-alkoxy, ou aryle; B est aryle facultativement substitué par halogène, amino, hydroxy, C1-6-alkyle, C1-6-alkoxy, ou aryle; D est amino facultativement substitué par halogène, amino, hydroxy, C1-6-alkyle, C1-6-alkoxy, ou aryle, ou sur un de leurs sels pharmacocompatibles.