3-(imidazol-1-yl)propyl isothiocyanate | 199522-85-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(imidazol-1-yl)propyl isothiocyanate
• 英文别名: 1-(3-isothiocyanatopropyl)imidazole
• CAS: 199522-85-5
• 化学式: C₇H₉N₃S
• mdl: MFCD25960704
• 分子量: 167.235
• InChiKey: MEQZNHSJODNALX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  62.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(imidazol-1-yl)propyl isothiocyanate 、 (4-氯苯氧基)-乙酸肼 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 1-(4-chlorophenoxyacetyl)-4-(3-imidazol-1-yl-propyl)-thiosemicarbazide
  参考文献：
  名称：

  Aggrecanase-2 inhibitors based on the acylthiosemicarbazide zinc-binding group

  摘要：

  Osteoarthritis is a disabling disease characterized by the articular cartilage breakdown. Aggrecanases are potential therapeutic targets for the treatment of this pathology. At the starting point of this project, an acylthiosemicarbazide was discovered to inhibit aggrecanase-2. The acylthiosemicarbazide Zn binding group is also a convenient linker for library synthesis. A focused library of 920 analogs was thus prepared and screened to establish structure-activity relationships. The modification of the acylthiosemicarbazide was also explored. This strategy combining library design and discrete compounds synthesis yielded inhibitor 35, that is highly selective for aggrecanases over a panel of metalloproteases and inhibits the degradation of native fully glycosylated aggrecan. A docking study generated binding conformations explaining the structure activity relationships. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.027
• 作为产物：
  描述：

  1-(3-氨基丙基)咪唑 、 二吡啶硫碳酸酯 以 二氯甲烷 为溶剂， 反应 24.0h， 以60%的产率得到3-(imidazol-1-yl)propyl isothiocyanate
  参考文献：
  名称：

  血红蛋白的区域选择性共价修饰，以寻找抗病药物。

  摘要：

  尽管镰状血红蛋白产生镰状细胞疾病的分子缺陷已经知道了数十年，但仍然没有有效的药物治疗作用于血红蛋白本身。在这项工作中，检查了一系列不同取代的异硫氰酸盐（R-NCS）与血红蛋白的区域选择性反应，试图改变镰刀型血红蛋白的溶解性。电喷雾质谱，分子建模，X射线晶体学和常规蛋白质化学用于研究这种区域选择性以及由此产生的修饰血红蛋白溶解度的增加。取决于所连接的R基团，发现异硫氰酸酯与Cysbeta93或α链的N端胺反应。该系列中最有效的化合物之一，2-（N，N-二甲基氨基）乙基异硫氰酸酯，与Cysbeta93的巯基发生选择性反应，后者与阳离子基团一起干扰了局部的血红蛋白结构。这种改性的HbS在完全脱氧状态下显示出约30％的溶解度增加，同时氧亲和力也显着增加。该化合物和相关的类似物似乎很容易穿过红细胞膜。讨论了这些结构变化与抑制胶凝的关系。增强HbS氧亲和力并直接抑制脱氧HbS聚合的双重活性，以及​​易

  DOI：

  10.1021/jm020361k

文献信息

• SEMISYNTHETIC DERIVATIVES OF NYSTATIN A1
  申请人：BLIRT S.A.

  公开号：US20150045316A1

  公开（公告）日：2015-02-12

  The invention provides semisynthetic derivatives of Nystatin A 1 , water soluble salts and complexes, pharmaceutical compositions and plant protection products comprising the derivatives and their use, as antifungal antibiotics (Formula 1a).

  这项发明提供了Nystatin A1的半合成衍生物，水溶性盐和络合物，包括这些衍生物的药物组合物和植物保护产品，以及它们作为抗真菌抗生素的用途（公式1a）。
• NOVEL GENES RELATED TO GLUTAMINYL CYCLASE
  申请人：Schilling Stephan

  公开号：US20080249083A1

  公开（公告）日：2008-10-09

  Novel glutaminyl-peptide cyclotransferase-like proteins (QPCTLs), which are isoenzymes of glutaminyl cyclase (QC, EC 2.3.2.5), and to isolated nucleic acids coding for these isoenzymes, all of which are useful for the discovery of new therapeutic agents, for measuring cyclase activity, and for determining the inhibitory activity of compounds against these glutaminyl cyclase isoenzymes.

  小说谷氨酰肽环转移酶样蛋白（QPCTLs），它们是谷氨酰环化酶（QC，EC 2.3.2.5）的同工酶，以及编码这些同工酶的分离核酸，所有这些对于发现新的治疗药物、测量环化酶活性以及确定化合物对这些谷氨酰环化酶同工酶的抑制活性都是有用的。
• 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、包含它们的组合物以及它们用于治疗与人类生长抑素受体亚型结合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.

  本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##或其药学上可接受的盐，该配体具有对生长抑素受体蛋白SSTR4的高和/或选择性亲和力，并用于制备治疗哺乳动物视网膜和/或虹膜睫状体不良病变相关疾病的药物。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、角膜炎、虹膜炎、视网膜炎、白内障和结膜炎等。
• Nonpeptide Somatostatin Agonists with sst₄ Selectivity:  Synthesis and Structure−Activity Relationships of Thioureas
  作者：Shenquan Liu、Cheng Tang、Bin Ho、Michael Ankersen、Carsten E. Stidsen、A. Michael Crider

  DOI：10.1021/jm980118e

  日期：1998.11.1

  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.