2,3-二氢化-2-硫代-4-噻唑乙酸 | 36365-79-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2,3-二氢化-2-硫代-4-噻唑乙酸
• 英文名称: (2-thioxo-2,3-dihydro-thiazol-4-yl)-acetic acid
• 英文别名: (2-Thioxo-2,3-dihydro-thiazol-4-yl)-essigsaeure；(2-thioxo-4-thiazolin-4-yl)acetic acid；4-Thiazoleacetic acid, 2,3-dihydro-2-thioxo-；2-(2-sulfanylidene-3H-1,3-thiazol-4-yl)acetic acid
• CAS: 36365-79-4
• 化学式: C₅H₅NO₂S₂
• mdl: MFCD07776885
• 分子量: 175.232
• InChiKey: VKONPNAILGGMSR-UHFFFAOYSA-N

物化性质

• 沸点：
  366.7±44.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2934100090

反应信息

• 作为反应物：
  描述：

  2,3-二氢化-2-硫代-4-噻唑乙酸 在 potassium carbonate 、 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 二氯甲烷 、 丁酮 为溶剂， 反应 24.0h， 生成 2-{2-[6,7-bis(2-methoxyethoxy)quinazolin-4-ylthio]thiazol-4-yl}-N-(3-chlorophenyl)acetamide
  参考文献：
  名称：

  Discovery of the Novel Potent and Selective FLT3 Inhibitor 1-{5-[7-(3- Morpholinopropoxy)quinazolin-4-ylthio]-[1,3,4]thiadiazol-2-yl}-3-p-tolylurea and Its Anti-Acute Myeloid Leukemia (AML) Activitiesin Vitroandin Vivo

  摘要：

  Structure-activity relationship (SAR) studies of 2-(quinazolin-4-ylthio)thiazole derivatives, which are for optimizing the in vitro and in vivo antiacute myeloid leukemia (AML) activity of a previously identified FLT3 inhibitor 2-(6,7-dimethoxyquinazolin-4-ylthio)thiazole (1), are described. SAR studies centering around the head (thiazole) and tails (6- and 7-positions) of the quinazoline moiety of 1 led to the discovery of a series of compounds that exhibited significantly dincreased potency against FLT3-driven AML MV4-11 cells. Preliminary in vivo assays were carried out on three highly active compounds, whose results showed that 1-{5-[7-(3-morpholinopropoxy)quinazolin-4-ylthio]-[1,3,4]thiadiazol-2-yl}-3-p-tolylurea (20c) had the highest in vivo activity. Further in vitro and in vivo anti-AML studies were then performed on 20c; in an MV4-11 xenograft mouse model, a once-daily dose of 20c at 100 mg/kg for 18 days led to complete tumor regression without obvious toxicity. Western blot and immunohistochemical analysis were carried out to illustrate the mechanism of action of 20c.

  DOI：

  10.1021/jm300042x
• 作为产物：
  描述：

  2,3-二氢-2-硫代-4-噻唑乙酸乙酯 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以63%的产率得到2,3-二氢化-2-硫代-4-噻唑乙酸
  参考文献：
  名称：

  IDO inhibitors

  摘要：

  目前提供的方法包括：(a) 调节吲哚胺2,3-二氧化酶的活性，包括将吲哚胺2,3-二氧化酶与本文描述的某一方面中描述的化合物的调节有效量接触；(b) 治疗需要吲哚胺2,3-二氧化酶（IDO）介导的免疫抑制的受试者，包括给予本文描述的某一方面中描述的化合物的有效吲哚胺2,3-二氧化酶抑制量；(c) 治疗受益于吲哚胺-2,3-二氧化酶酶活性抑制的医疗状况，包括给予本文描述的某一方面中描述的化合物的有效吲哚胺2,3-二氧化酶抑制量；(d) 增强抗癌治疗的有效性，包括给予抗癌药物和本文描述的某一方面中描述的化合物；(e) 治疗与癌症相关的肿瘤特异性免疫抑制，包括给予本文描述的某一方面中描述的化合物的有效吲哚胺2,3-二氧化酶抑制量；以及(f) 治疗与传染病相关的免疫抑制，例如HIV-I感染，包括给予本文描述的某一方面中描述的化合物的有效吲哚胺2,3-二氧化酶抑制量。

  公开号：

  US10047066B2

文献信息

• Cephem compounds and pharmaceutical use thereof
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US06150351A1

  公开（公告）日：2000-11-21

  This invention relates to new cephem compound represented by the following general formula (I): ##STR1## wherein each symbol is as defined in the specification or a salt thereof, which has antimicrobial activity against Helicobacter pylori, and are useful as anti-Helicobacter pylori agents, anti-gastritis agents, anti-ulcer agents and anti-cancer agents.

  本发明涉及一种由以下一般式（I）表示的新头孢素化合物：其中每个符号如规范中定义或其盐，具有抗幽门螺杆菌活性，并可用作抗幽门螺杆菌药物、抗胃炎药物、抗溃疡药物和抗癌药物。
• Carboxylic Acid Derivative Containing Thiazole Ring and Pharmaceutical Use Thereof
  申请人：Tozawa Takashi

  公开号：US20080167307A1

  公开（公告）日：2008-07-10

  According to the present invention, a compound represented by the following formula (I) having a superior PPAR α agonist action and concurrently showing a hypolipidemic action can be provided, and further, a compound useful as a synthetic intermediate for the compound can be provided.

  根据本发明，可以提供一种具有卓越的PPARα激动剂作用并同时显示降脂作用的化合物，该化合物表示为以下公式（I），并且还可以提供一种用作该化合物的合成中间体的化合物。
• Carboxylic acid derivative containing thiazole ring and pharmaceutical use thereof
  申请人：Mitsubishi Tanabe Pharma Corporation

  公开号：US08026370B2

  公开（公告）日：2011-09-27

  According to the present invention, a compound represented by the following formula (I) having a superior PPARα agonist action and concurrently showing a hypolipidemic action can be provided, and further, a compound useful as a synthetic intermediate for the compound can be provided.

  根据本发明，可以提供一种具有优异的PPARα激动剂作用并同时显示降脂作用的以下式（I）所表示的化合物，而且还可以提供一种作为该化合物的合成中间体有用的化合物。
• Thiazole- and imidazole-containing peptidomimetic inhibitors of protein farnesyltransferase
  作者：Cristiano Bolchi、Marco Pallavicini、Sergio K. Bernini、Giuseppe Chiodini、Alberto Corsini、Nicola Ferri、Laura Fumagalli、Valentina Straniero、Ermanno Valoti

  DOI：10.1016/j.bmcl.2011.07.003

  日期：2011.9

  Mimetics of the C-terminal CAAX tetrapeptide of Ras protein were designed replacing internal dipeptide AA with 4-amino-2-phenylbenzoic acid and cysteine (C) with 2-amino-4-thiazolyl-, 2-mercapto-4-thiazolyl-, 2-mercapto-4-imidazolyl- and 2-methylmercapto-4-thiazolyl-acetic or propionic acid. The compound in which C is replaced by 2-amino-4-thiazolylacetic acid inhibited FTase activity in the low nanomolar range and showed antiproliferative effect on rat aortic smooth muscle cells interfering with Ras farnesylation. On the basis of these results, 2-aminothiazole can be considered as an alternative to heterocycles, such as pyridine and imidazole, normally used in FTase inhibitors designed as non-thiol CAAX mimetics. (C) 2011 Elsevier Ltd. All rights reserved.
• Studies on anti-Helicobacter pylori agents. Part 3: A novel, efficacious cephem derivative, FR193879
  作者：Yoshiki Yoshida、Keiji Matsuda、Hiroshi Sasaki、Yoshimi Matsumoto、Satoru Matsumoto、Shuichi Tawara、Hisashi Takasugi

  DOI：10.1016/j.bmcl.2004.02.068

  日期：2004.5

  The synthesis, therapeutic efficacy against H. pylori, and preliminary safety of the novel cephem. derivative, FR193879 (8a) are described. Compound 8a having a (4-carbamoylmethylthiazol-2-yl)thio moiety at the 3-position and a phenylacetamido at the 7-position was found to have good safety showing a nontoxic dose of >100 mg/kg in dogs in a 4-week repeat dose toxicity study and extremely potent therapeutic efficacy against H. pylori, showing 30 times superior activity compared to AMPC, and did not display cross-resistance with CAM or MNZ. (C) 2004 Elsevier Ltd. All rights reserved.