ethyl 2-benzyl-1,3-thiazole-4-carboxylate | 83553-49-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 2-benzyl-1,3-thiazole-4-carboxylate
• 英文别名: ethyl 2-benzylthiazole-4-carboxylate；2-benzyl-4-carbethoxythiazole；2-benzyl-thiazole-4-carboxylic acid ethyl ester；2-Benzyl-thiazol-4-carbonsaeure-aethylester；ethyl 2-benzyl-thiazole-4-carboxylate；Methyl 2-Benzylthiazol-4-carbalalat
• CAS: 83553-49-5
• 化学式: C₁₃H₁₃NO₂S
• mdl: MFCD02102511
• 分子量: 247.318
• InChiKey: SJRIITISXFXAMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 储存条件：
  存储条件：室温、密封、干燥

反应信息

• 作为反应物：
  描述：

  ethyl 2-benzyl-1,3-thiazole-4-carboxylate 在 lithium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 生成 2-苄基-1,3-噻唑-4-羧酸
  参考文献：
  名称：

  Synthesis and Biological Investigation of Oxazole Hydroxamates as Highly Selective Histone Deacetylase 6 (HDAC6) Inhibitors

  摘要：

  Histone deacetylase 6 (HDAC6) catalyzes the removal of an acetyl group from lysine residues of several nonhistone proteins. Here we report the preparation of thiazole-, oxazole-, and oxadiazole-containing biarylhydroxamic acids by a short synthetic procedure. We identified them as selective HDAC6 inhibitors by investigating the inhibition of B recombinant HDAC enzymes and the protein acetylation in cells by Western blotting (tubulin vs histone acetylation). The most active compounds exhibited nanomolar potency and high selectivity for HDAC6. For example, an oxazole hydroxamate inhibits HDAC6 with an IC50 of 59 nM and has a selectivity index of >200 against HDAC1 and HDAC8. This is the first report showing that the nature of a heterocycle directly connected to a zinc binding group (ZBG) can be used to modulate subtype selectivity and potency for HDAC6 inhibitors to such an extent. We rationalize the high potency and selectivity of the oxazoles by molecular modeling and docking.

  DOI：

  10.1021/acs.jmedchem.5b01493
• 作为产物：
  描述：

  2-苯乙酰胺 在 tetraphosphorus decasulfide 作用下， 以 乙醇 、 苯 为溶剂， 反应 3.0h， 生成 ethyl 2-benzyl-1,3-thiazole-4-carboxylate
  参考文献：
  名称：

  (4R,5S)-Melithiazols F 和 I 的合成

  摘要：

  (2R,3S)-3-methylpenta-4-yne-1,2-diol (8) 的钯催化环化-甲氧基羰基化（8）衍生自 (2R,3S)-epoxybutanoate 7 然后甲基化得到四氢-2-furylidene乙酸酯 (-)-9，它被转化为左半醛 (+)-4。(+)-4 与衍生自联噻唑型碘化鏻 5 的磷酰酯之间使用双（三甲基甲硅烷基）酰胺锂进行 Wittig 反应，得到 (+)-(4R,5S)-甲基噻唑 F (1)，其光谱数据相同与天然产物 1. 此外，(+)-(4R,5S)-melithiazol I (2) 的合成采用与 (+)-(4R,5S)-melithiazol 相同的合成策略(1)。通过使用纸盘测定法评估合成的甲噻唑 F (1) 和 I (2) 对植物致病真菌辣椒疫霉的抗真菌活性。

  DOI：

  10.1002/ejoc.200500568

文献信息

• Solvent-free synthesis of bacillamide analogues as novel cytotoxic and anti-inflammatory agents
  作者：Sunil Kumar、Ranjana Aggarwal、Virender Kumar、Rachna Sadana、Bhumi Patel、Pawan Kaushik、Dhirender Kaushik

  DOI：10.1016/j.ejmech.2016.07.033

  日期：2016.11

  aryl/heteroaryl/amino/aminoarylthiazole-4-carboxamides as bacillamide analogues having structural variation at position-2 of thiazole ring. Bacillamide and its analogues were evaluated for their cytotoxic activity against three cancer cell lines (HCT-116, MDA-MD-231 and JURKAT cell lines) using colorimetric cell proliferation assay. Compounds 17a and 17b exhibited potent anti-cell proliferation activity

  bacillamide（一种海洋来源的生物活性类胰蛋白酶生物碱）的十四种类似物的合成已通过高效的收敛途径完成。本无溶剂方案涉及在初始步骤中形成噻唑环，然后在2-羟基-4,6存在下，取代的2-烷基/芳基/杂芳基/氨基/氨基芳基噻唑-4-羧酸乙酯与色胺之间进行酰胺偶联。 -二甲基嘧啶，一种固相催化剂，可产生N- [2-（1 H-吲哚-3-基）乙基] -2-烷基/芳基/杂芳基/氨基/氨基芳基噻唑-4-羧酰胺作为bacillamide类似物，在噻唑环的2位具有结构变化。使用比色细胞增殖测定法评估了巴西酰胺及其类似物对三种癌细胞系（HCT-116，MDA-MD-231和JURKAT细胞系）的细胞毒活性。化合物17a和17b对这些细胞系表现出有效的抗细胞增殖活性，IC 50值分别在〜3.0μM和〜0.1-0.6μM范围内。初步的作用机制研究表明，这些化合物可启动caspase依赖性细胞凋亡。另外，化合物16d，16f，17a和17d
• A concise and efficient route to the total synthesis of bacillamide A and its analogues
  作者：Sunil Kumar、Ranjana Aggarwal

  DOI：10.24820/ark.5550190.p010.362

  日期：——

  The synthesis of bacillamide A, a tryptamide alkaloid of marine origin, and its analogues from L-cysteine ethyl ester hydrochloride through an efficient and convergent synthetic approach is described in this work. The present two-step protocol involves the use of iodobenzene diacetate, a versatile oxidising agent, to synthesize the key intermediate ethyl 2-differently substituted-1,3-thiazole-4-carboxylates

  在这项工作中描述了 bacillamide A、一种海洋来源的色氨酸生物碱及其类似物从 L-半胱氨酸乙酯盐酸盐通过有效和收敛的合成方法合成。本两步协议涉及使用碘苯二乙酸酯，一种多功能氧化剂，一步合成关键中间体 2-不同取代-1,3-噻唑-4-羧酸乙酯。在这项工作中，4,6二甲基嘧啶-2-醇作为酯的无溶剂氨解催化剂，利用其同时给予和接受氢键的特性获得了标题化合物。
• Heterocyclic alcohols and their derivatives
  申请人：Roussel Uclaf

  公开号：US04501894A1

  公开（公告）日：1985-02-26

  Novel heterocyclic compounds of the formula ##STR1## wherein X is selected from the group consisting of chlorine, bromine, iodine and --OH, W is selected from the group consisting of hydrogen and --CN, Z is selected from the group consisting of --CH.sub.2 -- and --O-- attached to the carbon atom included between a nitrogen and the sulfur atom of Y and Y is selected from the group consisting of thiazolyl or thiadiazolyl connected to ##STR2## at one of its available positions except for (2-benzyl-4 and 5-thiazolyl) methanol and .alpha.-cyano-(2-benzyl-5-thiazolyl)-methanol and the compounds wherein X is halogen when W is --CN whose esters have insecticidal activity.

  该式的新颖杂环化合物为 ##STR1## 其中 X 从氯、溴、碘和—OH 组成的群体中选择，W 从氢和—CN 组成的群体中选择，Z 从连接到 Y 的氮和硫原子之间包括的碳原子上的—CH.sub.2—和—O—组成的群体中选择，Y 从连接到 ##STR2## 的噻唑基或噻二唑基中选择，除了(2-苄基-4和5-噻唑基)甲醇和.alpha.-氰基-(2-苄基-5-噻唑基)-甲醇以及当 W 为—CN 时 X 是卤素的化合物，其酯具有杀虫活性。
• Insecticidal esters
  申请人：Roussel Uclaf

  公开号：US04450169A1

  公开（公告）日：1984-05-22

  Novel esters of the formula ##STR1## wherein R is selected from the group consisting of ##STR2## W is selected from the group consisting of hydrogen and --CN, Z is selected from the group consisting of --CH.sub.2 -- and --O--, and is attached to a carbon atom included between a nitrogen and the sulfur atom of Y and Y is selected from the group consisting of thiazolyl or thiadiazolyl connected to ##STR3## at one of its available positions.

  公式为##STR1##的新型酯类，其中R从##STR2##组中选择，W从氢和--CN组中选择，Z从--CH.sub.2--和--O--组中选择，并附加到Y的氮和硫原子之间包括的碳原子上，Y从连接到##STR3##的噻唑基或噻二唑基组中选择其可用位置之一。
• Kim, Hong-Seok; Kwon, Il-Cheon; Kim, Oh-Hwoan, Journal of Heterocyclic Chemistry, 1995, vol. 32, # 3, p. 937 - 940
  作者：Kim, Hong-Seok、Kwon, Il-Cheon、Kim, Oh-Hwoan

  DOI：——

  日期：——