4-butyl isothiocyanate | 199522-80-0

• 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-butyl isothiocyanate
• 英文别名: 4-[N-(5-bromopyrid-2-yl)-N-(3,4-dichlorobenzyl)]aminobutyl isothiocyanate；5-bromo-N-[(3,4-dichlorophenyl)methyl]-N-(4-isothiocyanatobutyl)pyridin-2-amine
• CAS: 199522-80-0
• 化学式: C₁₇H₁₆BrCl₂N₃S
• 分子量: 445.21
• InChiKey: HHIQIMNFVAJMRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  4-butyl isothiocyanate 在 盐酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 10.0h， 生成 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-N-(4-氨基丁基)-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 4-butyl 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

• Somatostatin agonists and antagonists
  申请人：Novo Nordisk A/S

  公开号：US06127343A1

  公开（公告）日：2000-10-03

  The present invention relates to compounds, compositions containing them, and their use for treating medical disorders related to binding to human somatostatin receptor subtypes.

  本发明涉及化合物、含有这些化合物的组合物，以及它们用于治疗与结合到人类生长抑素受体亚型相关的医学疾病的用途。
• Use of somatostatin agonists and antagonists for treating diseases
  申请人：Novo Nordisk A/S

  公开号：US06159941A1

  公开（公告）日：2000-12-12

  The invention relates to the use of a somatostatin receptor ligand of nonpeptide origin, e.g. of the general formula Ia or Ib ##STR1## or a pharmaceutically acceptable salt thereof, which has high and/or selective affinity to the somatostatin receptor protein designated SSTR4 and, for the preparation of a medicament for the treatment of a disease associated with an adverse condition in the retina and/or iris-ciliary body of a mammal. Such conditions are high intraocular pressure (IOP) and/or deep ocular infections. The diseases which may be treated are e.g. glaucoma, stromal keratitis, iritis, retinitis, cataract and conjunctivitis.

  该发明涉及使用非肽源的生长抑素受体配体，例如一般式Ia或Ib##STR1##或其药用盐，其对生长抑素受体蛋白SSTR4具有高和/或选择性亲和力，并用于制备用于治疗哺乳动物视网膜和/或虹膜-睫状体中不良状况相关疾病的药物。这些疾病包括高眼压（IOP）和/或深部眼部感染。可以治疗的疾病包括青光眼、基质性角膜炎、虹膜炎、视网膜炎、白内障和结膜炎。
• 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