4-iodomethyl-2-methylthiazole | 105687-33-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-iodomethyl-2-methylthiazole
• 英文别名: 4-(Iodomethyl)-2-methylthiazole；4-(iodomethyl)-2-methyl-1,3-thiazole
• CAS: 105687-33-0
• 化学式: C₅H₆INS
• 分子量: 239.08
• InChiKey: RKNQMYMRIZMLDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  262.1±23.0 °C(Predicted)
• 密度：
  1.935±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-iodomethyl-2-methylthiazole 在 lithium hydroxide monohydrate 、 双氧水 、 sodium hexamethyldisilazane 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成
  参考文献：
  名称：

  Structure-based design, synthesis and biological evaluation of novel β-secretase inhibitors containing a pyrazole or thiazole moiety as the P3 ligand

  摘要：

  We describe structure-based design, synthesis, and biological evaluation of a series of novel inhibitors bearing a pyrazole (compounds 3a-h) or a thiazole moiety (compounds 4a-e) as the P3 ligand. We have also explored Boc-beta-amino-L-alanine as a novel P2 ligand. A number of inhibitors have displayed b-secretase inhibitory potency. Inhibitor 4c has shown potent BACE1 inhibitory activity, K-i = 0.25 nM, cellular EC50 of 194 nM, and displayed good selectivity over BACE2. A model of 4c was created based upon the X-ray structure of 2-bound beta-secretase which revealed critical interactions in the active site. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.11.087
• 作为产物：
  描述：

  4-(氯甲基)-2-甲基-1,3-噻唑 在 氢碘酸 、 sodium iodide 作用下， 反应 3.0h， 生成 4-iodomethyl-2-methylthiazole
  参考文献：
  名称：

  Kajigaeshi, Shoji; Kawano, Yoichi; Fujisaki, Shizuo, Heterocycles, 1985, vol. 23, # 12, p. 2995 - 2998

  摘要：

  DOI：

文献信息

• Development of potent macrocyclic inhibitors of genotype 3a HCV NS3/4A protease
  作者：Michael T. Rudd、John A. McCauley、Joseph J. Romano、John W. Butcher、Kimberly Bush、Charles J. McIntyre、Kevin T. Nguyen、Kevin F. Gilbert、Terry A. Lyle、M. Katharine Holloway、Bang-Lin Wan、Joseph P. Vacca、Vincenzo Summa、Steven Harper、Michael Rowley、Steven S. Carroll、Christine Burlein、Jillian M. DiMuzio、Adam Gates、Donald J. Graham、Qian Huang、Steven W. Ludmerer、Stephanie McClain、Carolyn McHale、Mark Stahlhut、Christine Fandozzi、Anne Taylor、Nicole Trainor、David B. Olsen、Nigel J. Liverton

  DOI：10.1016/j.bmcl.2012.08.106

  日期：2012.12

  A series of macrocyclic compounds containing 2-substituted-quinoline moieties have been discovered and shown to exhibit excellent HCV NS3/4a genotype 3a and genotype 1b R155K mutant activity while maintaining the high rat liver exposure. Cyclization of the 2-substituted quinoline substituent led to a series of tricyclic P2 compounds which also display superb gt3a potency. (C) 2012 Elsevier Ltd. All rights reserved.
• 9-Dihydroerythromycin ethers as motilin agonists—Developing structure–activity relationships for potency and safety
  作者：Yaoquan Liu、Yong Li、David C. Myles、Mark Claypool、Christopher W. Carreras、Simon J. Shaw

  DOI：10.1016/j.bmc.2010.08.035

  日期：2010.11

  A series of derivatives of the amine of 9-dihydro-9-O-ethylamino-N-desmethyl-N-isopropyl erythromycin A derivatives were synthesized as motilin agonists. The compounds were developed for potency without showing antibacterial activity and inhibition of the hERG potassium channel. The formamide of the amide series was found to show the optimal combination of properties relative to carbamates, ureas, thioureas, and amines. This prompted an investigation of heterocyclic isosteres for the amide. In this series the triazole had the optimal combination of properties. From the study, two compounds met the criteria for detailed pharmacokinetic studies. (C) 2010 Elsevier Ltd. All rights reserved.
• KAJIGAESHI, SHOJI;KAWANO, YOICHI;FUJISAKI, SHIZUO;KANEMADA, SHUJI, HETEROCYCLES, 1985, 23, N 12, 2995-2998
  作者：KAJIGAESHI, SHOJI、KAWANO, YOICHI、FUJISAKI, SHIZUO、KANEMADA, SHUJI

  DOI：——

  日期：——
• Structure-based design, synthesis and biological evaluation of novel β-secretase inhibitors containing a pyrazole or thiazole moiety as the P3 ligand
  作者：Arun K. Ghosh、Margherita Brindisi、Yu-Chen Yen、Xiaoming Xu、Xiangping Huang、Thippeswamy Devasamudram、Geoffrey Bilcer、Hui Lei、Gerald Koelsch、Andrew D. Mesecar、Jordan Tang

  DOI：10.1016/j.bmcl.2014.11.087

  日期：2015.2

  We describe structure-based design, synthesis, and biological evaluation of a series of novel inhibitors bearing a pyrazole (compounds 3a-h) or a thiazole moiety (compounds 4a-e) as the P3 ligand. We have also explored Boc-beta-amino-L-alanine as a novel P2 ligand. A number of inhibitors have displayed b-secretase inhibitory potency. Inhibitor 4c has shown potent BACE1 inhibitory activity, K-i = 0.25 nM, cellular EC50 of 194 nM, and displayed good selectivity over BACE2. A model of 4c was created based upon the X-ray structure of 2-bound beta-secretase which revealed critical interactions in the active site. (C) 2014 Elsevier Ltd. All rights reserved.
• Kajigaeshi, Shoji; Kawano, Yoichi; Fujisaki, Shizuo, Heterocycles, 1985, vol. 23, # 12, p. 2995 - 2998
  作者：Kajigaeshi, Shoji、Kawano, Yoichi、Fujisaki, Shizuo、Kanemasa, Shuji

  DOI：——

  日期：——