[(噻吩-2-羰基)氨基]乙酸甲酯 | 63203-31-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: [(噻吩-2-羰基)氨基]乙酸甲酯
• 英文名称: methyl 2-(thiophene-2-carboxamido)acetate
• 英文别名: methyl (thiophene-2-carbonyl)glycinate；methyl 2-(2-thienoylamino)acetate；2-thenoyl-Gly-OMe；N-(2-thenoyl)glycine methyl ester；methyl 2-(2-thenoylamino)acetate；[(Thiophene-2-carbonyl)amino] acetic acid methyl ester；methyl 2-(thiophene-2-carbonylamino)acetate
• CAS: 63203-31-6
• 化学式: C₈H₉NO₃S
• mdl: MFCD01213612
• 分子量: 199.23
• InChiKey: GCYJJPOBYJQNHH-UHFFFAOYSA-N

物化性质

• 保留指数：
  1674

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  83.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 储存条件：
  存放在2-8℃的环境中，应保持干燥并密封。

反应信息

• 作为反应物：
  描述：

  [(噻吩-2-羰基)氨基]乙酸甲酯 在 盐酸 、 一水合肼 、 sodium nitrite 作用下， 以 甲醇 、 水 、 溶剂黄146 为溶剂， 反应 24.08h， 生成 2-(thiophene-2-carbonylamino)acetyl azide
  参考文献：
  名称：

  El-Naggar; Aboul-Enein; Makhlouf, Journal of the Indian Chemical Society, 1982, vol. 59, # 6, p. 783 - 786

  摘要：

  DOI：
• 作为产物：
  描述：

  2-噻吩甲酰氯 在 硫酸 、 sodium hydroxide 作用下， 反应 3.0h， 生成 [(噻吩-2-羰基)氨基]乙酸甲酯
  参考文献：
  名称：

  Synthesis, biological activity screening and molecular modeling study of acylaminoacetamide derivatives

  摘要：

  In this study, non-rigid analogs of thalidomide have been designed in order to develop potentially active, more effective and safer lead molecules for disorders caused or contributed by inflammation. Five different series of acylaminoacetamide compounds were synthesized, and the biological inhibitory potency of the title compounds has been determined by evaluating their effects on COX-2 isoenzyme expression and PGE(2) production in A549 (human lung adenocarcinoma) cell lines. Among the studied series, N-[2-(isopropylamino)-2-oxoethyl]isonicotinamide is the most active inhibitory compound on COX-2 isoenzyme expression, and N-[2-oxo-2-(pyrolydine-1-yl)etyl]isonicotinamide is the most active inhibitory compound on the biosynthesis of PGE(2). Molecular docking studies and molecular dynamics simulations were also applied to investigate non-covalent interactions of the most active compounds inside the active side of the crystal structure of murine cyclooxygenase 2 (mCOX-2) isoenzyme.

  DOI：

  10.1007/s00044-015-1419-4

文献信息

• Heterocyclic compounds
  申请人：——

  公开号：US20030166697A1

  公开（公告）日：2003-09-04

  The present invention provides a preventive or therapeutic agent for hyperlipidemia, comprising as an active ingredient a heterocyclic compound of the formula [1], or a pharmaceutically acceptable salt thereof: R 1 -Het-D-E  [1] wherein: R 1 is optionally substituted aryl or aromatic heterocyclic group, Het is a divalent aromatic heterocyclic group, D is alkylene, alkenylene, alkynylene, or the like, and E is carboxy, or the like, and novel compounds among the heterocyclic compounds of the formula [1] above, which has blood triglyceride lowering effect, LDL-C lowering effect, and blood glucose lowering effect and blood insulin lowering effect, or HDL-C increasing effect or atherogenic index lowering effect all together, and hence is useful in the prevention or treatment of hyperlipidemia, arteriosclerosis, diabetes mellitus, hypertension, obesity, and the like.

  本发明提供了一种用于高脂血症的预防或治疗剂，其活性成分为式[1]所示的杂环化合物或其药学上可接受的盐：R1-Het-D-E [1]其中：R1为任选取代的芳基或芳香性杂环基团，Het为二价芳香性杂环基团，D为亚烷基、亚烯基、亚炔基等，E为羧基等，以及上述式[1]所示杂环化合物中的新型化合物，其具有降低血液甘油三酯、降低LDL-C、降低血糖、降低血液胰岛素、增加HDL-C或降低动脉粥样硬化指数的效果，因此可用于预防或治疗高脂血症、动脉硬化、糖尿病、高血压、肥胖等疾病。
• Furan- and Thiophene-2-Carbonyl Amino Acid Derivatives Activate Hypoxia-Inducible Factor via Inhibition of Factor Inhibiting Hypoxia-Inducible Factor-1
  作者：Shin-ichi Kawaguchi、Yuhei Gonda、Takuya Yamamoto、Yuki Sato、Hiroyuki Shinohara、Yohsuke Kobiki、Atsuhiko Ichimura、Takashi Dan、Motohiro Sonoda、Toshio Miyata、Akiya Ogawa、Tadayuki Tsujita

  DOI：10.3390/molecules23040885

  日期：——

  To activate HIF exogenously, without exposing cells to hypoxic conditions, many small-molecule inhibitors targeting prolyl hydroxylase domain-containing protein have been developed. In addition, suppression of factor inhibiting HIF-1 (FIH-1) has also been shown to have the potential to activate HIF-α. However, few small-molecule inhibitors of FIH-1 have been developed. In this study, we synthesized

  一系列抗缺氧蛋白的诱导可在暴露于缺氧条件下保护细胞。缺氧诱导因子-α（HIF-α）是协调这种保护作用的主要转录因子。为了在不使细胞暴露于低氧条件下外源激活HIF，已经开发了许多靶向含脯氨酰羟化酶结构域蛋白的小分子抑制剂。此外，抑制因子HIF-1（FIH-1）的抑制也被证明具有激活HIF-α的潜力。但是，很少开发出FIH-1的小分子抑制剂。在这项研究中，我们合成了一系列具有抑制FIH-1潜力的呋喃和噻吩-2-羰基氨基酸衍生物。通过测量HIF响应元件（HRE）启动子活性，在SK-N-BE（2）c细胞中评估了这些化合物的抑制活性。
• Magnetic CuFe2O4 nanoparticles: a retrievable catalyst for oxidative amidation of aldehydes with amine hydrochloride salts
  作者：A. Suresh Kumar、B. Thulasiram、S. Bala Laxmi、Vikas S. Rawat、B. Sreedhar

  DOI：10.1016/j.tet.2014.01.051

  日期：2014.9

  for the oxidative amidation of aldehydes with amine hydrochloride salts is described. A wide range of amides have been synthesized in good to excellent yields under mild conditions. Chiral amide also synthesized from its corresponding chiral amine salt with retention of the stereochemistry. In particular, the performance of the magnetic separation of the catalyst was very efficient and an alternative

  描述了磁性CuFe 2 O 4纳米颗粒在醛与胺盐酸盐的氧化酰胺化中的应用。在温和的条件下，已经以良好的收率合成了各种酰胺。还从其相应的手性胺盐合成了手性酰胺，并且保留了立体化学。特别地，催化剂的磁分离性能非常有效，并且可以替代时间，溶剂和耗能的分离程序。连续五个周期后，催化剂的催化活性保持不变，由于其效率，易处理性和成本效益，使其在环境方面无害且可广泛应用。
• Tetrazoleacetic acid derivatives and use for aldose reductase inhibitory
  申请人：Wakamoto Pharmaceutical Co., Ltd.

  公开号：US05068239A1

  公开（公告）日：1991-11-26

  A tetrazoleacetic acid derivative represented by the following general formula (I): ##STR1## [in Formula (I), R.sub.1 represents a hydrogen atom or an alkyl group; R.sub.2 represents a hydrogen atom, an alkyl group, an aralkyl group, a halogen atom, a haloalkyl group, a hydroxyl group, an alkoxy group, an alkoxyalkyl group, an amino group, an aryl group, an alkyl or aryl thio group, an alkyl or aryl carbonylamino group, an alkyl or aryl sulfonylamino group, an alkyl or aryl aminosulfonyl group, an alkyl or aryl sulfonyl group or an alkyl or aryl sulfinyl group; and X represents --O-- or --S--] except for [5-(2-thienyl)tetrazol-1-yl] acetic acid, [5-(2-furyl)tetrazol-1-yl] acetic acid and ethyl esters thereof, or a salt thereof shows excellent aldose reductase inhibitory activity, has low toxicity to organisms and is quite effective as an essential component of a preventive medicine and/or remedy for diabetic complications.

  以下是通式（I）所代表的四唑乙酸衍生物：##STR1## [在通式（I）中，R.sub.1代表氢原子或烷基；R.sub.2代表氢原子、烷基、芳基烷基、卤素原子、卤代烷基、羟基、烷氧基、烷氧基烷基、氨基、芳基、烷基或芳基硫基、烷基或芳基羰基氨基、烷基或芳基磺酰氨基、烷基或芳基氨基磺酰基、烷基或芳基磺酰基氨基、烷基或芳基亚磺酰基或烷基或芳基亚磺酰基；X代表--O--或--S--]除了[5-(2-噻吩基)四唑-1-基]乙酸、[5-(2-呋喃基)四唑-1-基]乙酸和其乙酯，或其盐，表现出优异的醛糖还原酶抑制活性，对生物的毒性低，是预防糖尿病并发症的重要组成部分和/或治疗药物的有效成分。
• HETEROCYCLIC COMPOUNDS
  申请人：Nippon Shinyaku Co., Ltd.

  公开号：EP1295875A1

  公开（公告）日：2003-03-26

  The present invention provides a preventive or therapeutic agent for hyperlipidemia, comprising as an active ingredient a heterocyclic compound of the formula [1] or a pharmaceutically acceptable salt thereof:         R1―Het―D―E     [1] wherein: R1 is optionally substituted aryl or aromatic heterocyclic group, Het is a divalent aromatic heterocyclic group, D is alkylene, alkenylene, alkynylene, or the like, and E is carboxy, or the like, and novel compounds among the heterocyclic compounds of the formula [1] above, which has blood triglyceride lowering effect, LDL-C lowering effect, and blood glucose lowering effect and blood insulin lowering effect, or HDL-C increasing effect or atherogenic index lowering effect all together, and hence is useful in the prevention or treatment of hyperlipidemia, arteriosclerosis, diabetes mellitus, hypertension, obesity, and the like.

  本发明提供了一种预防或治疗高脂血症的药物，其活性成分包括式 [1] 的杂环化合物或其药学上可接受的盐： R1-Het-D-E [1] 其中 R1为任选取代的芳基或芳香杂环基团，Het为二价芳香杂环基团，D为亚烷基、亚烯基、亚炔基或类似基团，E为羧基或类似基团，上述式[1]杂环化合物中的新型化合物，具有降血甘油三酯作用、低密度脂蛋白胆固醇（LDL-C）降低效果、血糖降低效果和血胰岛素降低效果，或高密度脂蛋白胆固醇（HDL-C）增加效果或动脉粥样硬化指数降低效果，因此可用于预防或治疗高脂血症、动脉硬化、糖尿病、高血压、肥胖症等。