5-苄基-4-甲基-2-氨基噻唑 | 65248-93-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-苄基-4-甲基-2-氨基噻唑
• 英文名称: 5-benzyl-4-methyl-2-aminothiazole
• 英文别名: 5-benzyl-4-methyl-2-thiazolamine；5-benzyl-4-methylthiazol-2-amine；2-Amino-5-benzyl-4-methyl-thiazol；2-Amino-4-methyl-5-benzyl-thiazol；4-methyl-5-(phenylmethyl)-1,3-thiazol-2-amine；5-benzyl-4-methyl-thiazol-2-ylamine；5-Benzyl-4-methyl-1,3-thiazol-2-amine
• CAS: 65248-93-3
• 化学式: C₁₁H₁₂N₂S
• mdl: MFCD11186841
• 分子量: 204.296
• InChiKey: GBLYPAAOJUDNKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-苄基-4-甲基-2-氨基噻唑 、 3-环己基丙酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以51%的产率得到N-(5-benzyl-4-methylthiazol-2-yl)-3-cyclohexylpropanamide
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of aminothiazole derivatives against the fungal pathogens Histoplasma capsulatum and Cryptococcus neoformans

  摘要：

  Invasive fungal disease constitutes a growing health burden and development of novel antifungal drugs with high potency and selectivity against new fungal molecular targets are urgently needed. Previously, an aminothiazole derivative, designated as 41F5, was identified in our laboratories as highly active against Histoplasma yeast (MIC50 0.4-0.8 mu M) through phenotypic high-throughput screening of a commercial library of 3600 purine mimicking compounds (Antimicrob. Agents Chemother. 2013, 57, 4349). Consequently, 68 analogues of 41F5 were designed and synthesized or obtained from commercial sources and their MIC(50)s of growth inhibition were evaluated in Histoplasma capsulatum to establish a basic structure-activity-relationship (SAR) for this potentially new class of antifungals. The growth inhibiting potentials of smaller subsets of this library were also evaluated in Cryptococcus neoformans and human hepatocyte HepG2 cells, the latter to obtain selectivity indices (SIs). The results indicate that a thiazole core structure with a naphth-1-ylmethyl group at the 5-position and cyclohexylamide-, cyclohexylmethylamide-, or cyclohexylethylamide substituents at the 2-position caused the highest growth inhibition of Histoplasma yeast with MIC(50)s of 0.4 mu M. For these analogues, SIs of 92 to > 100 indicated generally low host toxicity. Substitution at the 3- and 4-position decreased antifungal activity. Similarities and differences were observed between Histoplasma and Cryptococcus SARs. For Cryptococcus, the naphth-1-ylmethyl substituent at the 5-position and smaller cyclopentylamide- or cyclohexylamide groups at the 2-position were important for activity. In contrast, slightly larger cyclohexylmethyl- and cyclohexylethyl substituents markedly decreased activity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.12.006
• 作为产物：
  描述：

  1-(5-benzyl-4-methylthiazol-2-yl)-2,5-dimethylpyrrole 在 盐酸羟胺 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以63%的产率得到5-苄基-4-甲基-2-氨基噻唑
  参考文献：
  名称：

  Bruekelman, Stephen P.; Leach, (Miss) Susan E.; Meakins, G. Denis, Journal of the Chemical Society. Perkin transactions I, 1984, p. 2801 - 2807

  摘要：

  DOI：

文献信息

• Iridium-Catalyzed 1,3-Hydrogen Shift/Chlorination of Allylic Alcohols
  作者：Nanna Ahlsten、Antonio Bermejo Gómez、Belén Martín-Matute

  DOI：10.1002/anie.201301013

  日期：2013.6.10

  Tandem: Allylic alcohols react with N‐chlorosuccinimide (NCS) in a tandem 1,3‐H shift/CCl bond formation leading to α‐chloroketones and α‐chloroaldehydes. The reactions proceed with complete selectivity to give single constitutional isomers of monochlorinated carbonyl compounds. The utility of the transformation is illustrated by the straightforward synthesis of 4,5‐disubstituted 2‐aminothiazoles

  串联：烯丙醇与N-氯代琥珀酰亚胺 (NCS) 串联 1,3-H 位移/C - Cl 键形成反应，生成 α-氯酮和 α-氯醛。反应完全选择性地进行，得到单氯化羰基化合物的单一结构异构体。从烯丙醇直接合成 4,5-二取代 2-氨基噻唑说明了该转化的实用性。
• [EN] N-THIAZOLYL-1, 2, 3, 4-TETRAHYDRO-6-ISOQUINOLINECARBOXAMIDE DERIVATIVES AS INHIBITORS OF STEAROYL COENZYME A DESATURASE<br/>[FR] DÉRIVÉS DE N-THIAZOLYL-1, 2, 3, 4-TÉTRAHYDRO-6-ISOQUINOLINE CARBOXAMIDE COMME INHIBITEURS DE LA STÉAROYLE COA DÉSATURASE
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2009150196A1

  公开（公告）日：2009-12-17

  The present invention relates to substituted thiazole compounds of the formula (I) wherein Z represents (A), (B), (C) and (D) where * represents the point of attachment and salts thereof, to pharmaceutical compositions containing them and their use in medicine. In particular, the invention relates to compounds for inhibiting SCD activity.

  本发明涉及式(I)的取代噻唑化合物，其中Z代表(A)、(B)、(C)和(D)，其中*代表连接点及其盐，以及含有它们的药物组合物和它们在医学上的应用。具体而言，该发明涉及抑制SCD活性的化合物。
• Yellow Dye and a Process for Ink Jet Printing Using the Dye
  申请人：Wright Gavin

  公开号：US20090142553A1

  公开（公告）日：2009-06-04

  A process for printing an image on a substrate comprising applying thereto by means of an ink jet printer an ink comprising a compound of Formula (1): wherein one of A and B is an optionally substituted heteroaryl group containing a ring sulphur atom and the other is an optionally substituted aryl or heteroaryl group and R 1 , X and Y are as specified. Also claimed are compounds of Formula (1) and various compositions containing the same.

  一种在基底上印刷图像的方法，包括通过喷墨打印机将化合物公式（1）的油墨施加在基底上：其中A和B中的一个是含有环硫原子的可选择取代的杂环芳基团，另一个是可选择取代的芳基或杂环芳基团，R1，X和Y如所述。还声明了公式（1）的化合物和包含其的各种组合物。
• One-Pot Syntheses of Substituted 2-Aminothiazoles and 2-Aminoselenazoles via Meerwein Arylation of Alkyl Vinyl Ketones
  作者：Yurii V. Ostapiuk、Andreas Schmidt、Mary Y. Ostapiuk、Oksana V. Barabash、Mykola Kravets、Colin Herzberger、Jan C. Namyslo、Mykola D. Obushak

  DOI：10.1055/s-0041-1738070

  日期：2022.8

  Both one-pot and two-step procedures for the synthesis of substituted 2-aminothiazoles and 2-aminoselenazoles are described. Anilines are first converted into arenediazonium bromides, which are then reacted with methyl vinyl ketone or cyclopropyl vinyl ketone in the presence of copper(II) bromide to give 4-aryl-3-bromobutan-2-ones (40–71%) and 3-aryl-2-bromo-1-cyclopropylpropan-1-ones (41–79%), respectively

  描述了合成取代的 2-氨基噻唑和 2-氨基硒唑的一锅法和两步法。首先将苯胺转化为溴化芳基重氮，然后在溴化铜 (II) 存在下与甲基乙烯基酮或环丙基乙烯基酮反应生成 4-aryl-3-bromobutan-2-ones (40–71%) 和 3 -aryl-2-bromo-1-cyclopropylpropan-1-ones (41–79%)，分别。这些产物在没有预先分离的情况下与硫脲或硒脲反应以制备4-甲基-和4-环丙基-5-(R-苄基)噻唑-2-胺(14个实施例)及其硒类似物(14个实施例)。一锅法的产率（40-81%）高于两步法的产率（32-70%）。
• Kopp, Bulletin de la Societe Chimique de France, 1950, p. 582
  作者：Kopp

  DOI：——

  日期：——