2-氨基-5-苄基-1,3-噻唑-4-酮 | 14230-00-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氨基-5-苄基-1,3-噻唑-4-酮
• 英文名称: (Z)-2-amino-5-benzylidenethiazol-4(5H)-one
• 英文别名: Xanthine oxidase-IN-10；(5Z)-5-benzylidene-2-imino-1,3-thiazolidin-4-one
• CAS: 14230-00-3
• 化学式: C₁₀H₈N₂OS
• mdl: MFCD00518974
• 分子量: 204.252
• InChiKey: SRILECHSVYTLLS-VURMDHGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2934100090

反应信息

• 作为反应物：
  描述：

  2-氨基-5-苄基-1,3-噻唑-4-酮 、 聚合甲醛 以72%的产率得到
  参考文献：
  名称：

  SOLOVEVA-YAVITS S. YU.; RAMSH S. M.; SMORYGO N. A.; GINAK A. I.; SOCHILIN+, XIMIYA GETEROTSIKL. SOED., 1980, HO 7, 929-932

  摘要：

  DOI：
• 作为产物：
  描述：

  3-phenylpropenoylthiourea 在 溴 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以70%的产率得到2-氨基-5-苄基-1,3-噻唑-4-酮
  参考文献：
  名称：

  Kutschy, Peter; Dzurilla, Milan; Kristian, Pavol, Collection of Czechoslovak Chemical Communications, 1981, vol. 46, # 2, p. 436 - 445

  摘要：

  DOI：

文献信息

• Discovery of (<i>Z</i>)-5-(4-Methoxybenzylidene)thiazolidine-2,4-dione, a Readily Available and Orally Active Glitazone for the Treatment of Concanavalin A-Induced Acute Liver Injury of BALB/c Mice
  作者：Youfu Luo、Liang Ma、Hao Zheng、Lijuan Chen、Rui Li、Chunmei He、Shengyong Yang、Xia Ye、Zhizhi Chen、Zicheng Li、Yan Gao、Jing Han、Gu He、Li Yang、Yuquan Wei

  DOI：10.1021/jm901183d

  日期：2010.1.14

  that oral administration of 2g, 2h, 4f, or 6h decreases, most significantly for 4f, the serum levels of alanine aminotransaminase (ALT) and asparate aminotransaminase (AST) in ConA-induced acute livery injury BALB/c mice. Histopathological evaluation liver sections confirmed 4f as a potent, orally active compound for hepatoprotective effects against ConA-induced acute liver injury in BALB/c mice.

  大量证据表明，单核细胞/巨噬细胞浸润与多种炎性疾病有关，包括急性肝损伤。单核细胞趋化蛋白1（MCP-1）在巨噬细胞募集过程中起着至关重要的作用。我们在此提出了一种小分子文库和一种可行的快速筛选方法，用于评估抑制MCP-1刺激的RAW264.7细胞趋化性的能力。合成和筛选了53个小分子，四种化合物（2g，2h，4f和6h）显示出抑制作用，IC 50值范围为0.72至20.47μM，使用化合物4f是最有效的。进一步的体内研究表明，口服2g，2h，4f或6h可降低ConA诱导的急性肝损伤BALB / c小鼠的丙氨酸氨基转氨酶（ALT）和天冬酰胺转氨酶（AST）的血清水平，尤其是在4f时。组织病理学评估肝脏切片证实4f是一种有效的口服活性化合物，具有抗ConA诱导的BALB / c小鼠急性肝损伤的肝保护作用。
• Traceless solid-phase synthesis of 2-amino-5-alkylidene-thiazol-4-ones
  作者：Maurizio Pulici、Francesca Quartieri

  DOI：10.1016/j.tetlet.2005.02.059

  日期：2005.4

  2-Amino-5-alkylidene-thiazol-4-ones bearing two diversity points are prepared by a solid-phase strategy exploiting rhodanine as the starting material. Rhodanine is first loaded on bromo-Wang resin, subjected to Knovenagel condensation with aldehydes, and cleaved off the resin in a traceless manner by means of an amine.

  通过以罗丹宁为原料的固相策略制备具有两个多样性点的2-氨基-5-亚烷基-噻唑-4-酮。首先将罗丹宁负载在溴旺树脂上，使其与醛进行Knovenagel缩合，然后借助胺以无痕方式将其裂解。
• Synthesis and biological evaluation of some new Thiazolo[3,2-a][1,3,5]triazine derivatives
  作者：Wafaa S. Hamama、Mohamed A. Ismail、Saad Shaaban、Hanafi H. Zoorob

  DOI：10.1007/s00044-011-9783-1

  日期：2012.9

  Abstract 2-Iminothiazolidin-4-one ( 1 ) was utilized for the synthesis of several new thiazolo[3,2- a ][1,3,5]triazine derivatives. 3-Phenyl-3,4-dihydro-2 H -thiazolo[3,2- a ][1,3,5]triazin-6(7 H )-one ( 2 ) was prepared according to Mannich procedure. Both compounds 1 and 2 reacted with aromatic aldehydes to afford arylidene derivatives 3 – 7 . Compounds 5 – 7 were obtained through another two routes

  摘要 2-Iminothiazolidin-4-one（ 1 ）用于合成几种新的噻唑并[3,2- a ] [1,3,5]三嗪衍生物。根据曼尼希方法制备3-苯基-3,4-二氢-2 H- 噻唑并[3,2- a ] [1,3,5]三嗪-6（7 H ）-一（ 2 ）。两种化合物 1 和 2 与芳香醛反应，得到亚芳基衍生物 3 - 7 。化合物 5 - 7 是通过制备的另外两个途径获得，首先施加曼尼希反应的化合物时 3 和 4 通过使化合物和第二 2 用活化的烯烃 11 由三乙胺催化，另外，反应 2 与 双 亚芳基 16 ，得到化合物 18 。化合物 2 与单和二芳族重氮盐两者反应以分别提供2-芳基-偶氮噻唑并[3，2- a ]三嗪 20 和 21 或双[2-偶氮噻唑并[3，2- a ]三嗪]亚苯基 22 。硫氨甲酰基衍生物 25 和 26 通过活性亚甲基和亚氨基的反应中制备 1 分别与异硫氰酸苯酯
• Design, synthesis, and pharmacological evaluation of N-(4-mono and 4,5-disubstituted thiazol-2-yl)-2-aryl-3-(tetrahydro-2H-pyran-4-yl)propanamides as glucokinase activators
  作者：Fuying Li、Qingzhang Zhu、Yi Zhang、Ying Feng、Ying Leng、Ao Zhang

  DOI：10.1016/j.bmc.2010.04.038

  日期：2010.6.1

  A series of N-thiazole substituted arylacetamides were designed on the basis of metabolic mechanism of the aminothiazole fragment as glucokinase (GK) activators for the treatment of type 2 diabetes. Instead of introducing a substituent to block the metabolic sensitive C-5 position on the thiazole core directly, a wide variety of C-4 or both C-4 and C-5 substitutions were explored. Compound R-9k bearing an iso-propyl group as the C-4 substituent was found possessing the highest GK activation potency with an EC50 of 0.026 mu M. This compound significantly increased both glucose uptake and glycogen synthesis in rat primary cultured hepatocytes. Moreover, single oral administration of compound R-9k exerted significant reduction of blood glucose levels in both ICR and ob/ob mice. These promising results indicated that compound R-9k is a potent orally active GK activator, and is warranted for further investigation as a new antidiabetic treatment. (C) 2010 Elsevier Ltd. All rights reserved.
• Thermal degradation of some coordination polymers
  作者：Narayan S. Bhave、Vaidyanathan N. Iyer

  DOI：10.1007/bf01913337

  日期：1987.9