5-苯基-2-噻吩羧酸乙酯 | 19282-39-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 5-苯基-2-噻吩羧酸乙酯
• 英文名称: ethyl 5-phenylthiophene-2-carboxylate
• CAS: 19282-39-4
• 化学式: C₁₃H₁₂O₂S
• mdl: MFCD01860759
• 分子量: 232.303
• InChiKey: UXNYFCYTHBUYNK-UHFFFAOYSA-N

物化性质

• 熔点：
  31-33°
• 沸点：
  364.6±30.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5-苯基-2-噻吩羧酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以75%的产率得到5-phenylthiophene-2-carbohydrazide
  参考文献：
  名称：

  Synthesis, cytotoxicity and effects of some 1,2,4-triazole and 1,3,4-thiadiazole derivatives on immunocompetent cells

  摘要：

  Novel derivatives of 4,5-substituted-1,2,4-triazole-thiones and 2,5-substituted-1,3,4-thiadiazoles were synthesized and evaluated for their cytotoxicity. The biological study indicated that compounds 4-ethyl-5-(4,5,6,7-tetrahydro-1-benzothien-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 13, N-ethyl-5-(4,5,6,7-tetrahydro-1-benzothien-2-yl)-1,3,4-thiadiazol-2-amine 16, 4-amino-5-(4,5,6,7-tetrahydro-1-benzothien-2-yl)-2, 4-dihydro-3H-1,2,4-triazole-3-thione 20 and 4-amino-5-(5-phenylthien-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 21 possessed high cytotoxicity in vitro against thymocytes, The corresponding IC50 values were 0.46 mu M, 5.2 x 10(-6) mu M, 0.012 mu M and 1.0 x 10(-6) mu M. Most toxic against lymphocytes was compound 21, IC50 - 0.012 mu M. The tested compounds showed a general stimulation effect on B-cells' response. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.03.006
• 作为产物：
  描述：

  苯乙酮 在 sodium 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 3.83h， 生成 5-苯基-2-噻吩羧酸乙酯
  参考文献：
  名称：

  含哌嗪腙结构的噁唑烷酮类化合物

  摘要：

  本发明公开一种含哌嗪腙结构的噁唑烷酮类化合物，包括含通式(Ⅰ)的化合物、或其立体异构体、或其药学上可接受的盐、或其溶剂化物、或其前药；其中，R1为氢、氟、氯或三氟甲基；R2为‑NHCOCH3或‑OH；R3为Ar、Ar为任意1‑3个R4取代的C5‑C10芳基及杂芳基；R4为氢，羟基，卤素，硝基，氨基，氰基，C1‑C6烷基，C1‑C6烷氧基，任选被羟基、氨基或卤代的C1‑C6烷基，任选被羟基、氨基或卤代的C1‑C6烷氧基，被单或二(C1‑C6烷基)取代的氨基，C1‑C6烷基酰胺基，游离的、成盐的、酯化的和酰胺化的羧基，C1‑C6烷基亚磺酰基，C1‑C6烷基磺酰基，C1‑C6烷基酰基，氨基甲酰基。该化合物可用于制备治疗微生物感染的药物。

  公开号：

  CN107033095B

文献信息

• [EN] URIDINE NUCLEOSIDE DERIVATIVES, COMPOSITIONS AND METHODS OF USE<br/>[FR] DÉRIVÉS D'URIDINE NUCLÉOSIDE, COMPOSITIONS ET PROCÉDÉS D'UTILISATION
  申请人：UNIV TUFTS

  公开号：WO2018058148A1

  公开（公告）日：2018-03-29

  This disclosure relates to uridine nucleoside derivatives, compositions comprising therapeutically effective amounts of those nucleoside derivatives and methods of using those nucleoside derivatives or compositions in treating disorders that are responsive to compounds, such as agonists, of P2Y6 receptor, e.g., neuronal disorders, including neurodegenerative disorders (e.g., Alzheimer's disease, Parkinson's disease) and traumatic CNS injury, pain, Down Syndrome (DS), glaucoma and inflammatory conditions.

  这项披露涉及尿苷核苷衍生物，包含治疗有效量的这些核苷衍生物的组合物，以及使用这些核苷衍生物或组合物治疗对P2Y6受体的化合物（如激动剂）具有反应的疾病的方法，例如神经疾病，包括神经退行性疾病（如阿尔茨海默病、帕金森病）和创伤性中枢神经系统损伤、疼痛、唐氏综合症（DS）、青光眼和炎症性疾病。
• The conversions of isothiazolium salts into thiophenecarboxylic ester derivatives
  作者：David M. McKinnon、K. Ann Duncan、Lesley M. Millar

  DOI：10.1139/v84-271

  日期：1984.8.1

  Several 3-aminothiophene-2-carboxylic ester derivatives are made by reaction of potassium 3-ethoxy-3-oxopropanoate with isothiazolium salts or by reaction with 2-ethoxy-2-oxoethylidenedimethylsulfurane. In the latter case deaminated products are also isolated. These products are consistent with initial nucleophilic attack on the sulfur atom of the isothiazolium salt. In one case a pyrrole derivative is formed by a novel rearrangement of an intermediate aziridine derivative. Some further derivatives of 3-benzylaminobenzo[b]thiophene are described.

  通过将钾3-乙氧基-3-氧代丙酸酯与异噻唑盐反应或与2-乙氧基-2-氧代乙基亚甲基二甲基硫烷反应，制备了几种3-氨基噻吩-2-羧酸酯衍生物。在后一种情况下，还分离出去氨基产物。这些产物与异噻唑盐的硫原子的初始亲核攻击一致。在一个案例中，通过中间环氮烷衍生物的新颖重排形成吡咯衍生物。还描述了一些3-苄基氨基苯并[b]噻吩的进一步衍生物。
• Base catalyzed reaction of ethyl thioglycolate with β-aryl-β-(methylthio) acroleins: a general method for the synthesis of 2-carbethoxy-5-substituted/4,5-annulated thiophenes in high overall yields
  作者：G. Byre Gowda、C.S. Pradeepa kumara、N. Ramesh、M.P. Sadashiva、H. Junjappa

  DOI：10.1016/j.tetlet.2016.01.055

  日期：2016.2

  were shown to be stable unlike their counterpart the chloroacroleins and their efficacy as 1,3-dielectrophilic properties have now been examined successfully in this work. They are shown to react with ethyl thioglycolate in the presence of anhydrous potassium carbonate in boiling ethanol to yield the corresponding 5-substituted/4,5-annulated-2-carbethoxy thiophenes in 70–80% overall high yields.

  已证明（甲硫基）丙烯醛1a - m是稳定的，不同于其对应的氯丙烯醛，并且已成功地检测了它们作为1,3-二亲电子性质的功效。它们在无水碳酸钾存在下于沸腾的乙醇中与硫代乙醇酸乙酯反应，可产生相应的5-取代/ 4,5-环化-2-羰基乙氧基噻吩，总产率为70-80％。
• Programmed Synthesis of Tetra-Aryl Thiophenes with Stepwise, Ester-Controlled Regioselectivity
  作者：Cynthia Messina、Xavier Ottenwaelder、Pat Forgione

  DOI：10.1021/acs.orglett.1c02447

  日期：2021.10.1

  Herein, we report a modular synthetic route to access tetra-arylated thiophene compounds with four different substituents with programmed chemical control provided by an ester activating/directing group. This method enables the functionalization of individual positions of thiophene sequentially via regioselective halogenations and cross-coupling reactions. The reaction sequence described provides tetra-arylated

  在此，我们报告了一种模块化合成路线，以通过酯活化/导向基团提供的程序化化学控制来获得具有四种不同取代基的四芳基化噻吩化合物。该方法能够通过区域选择性卤化和交叉偶联反应顺序地对噻吩的各个位置进行功能化。所描述的反应顺序以比以前的路线更高的产率提供了四芳基噻吩，并采用了实用的反应方案、简单的催化系统和较短的反应时间。
• Thiophene and Benzothiophene Hydroxamic Acid Derivatives
  申请人：Miller A. Thomas

  公开号：US20070213392A1

  公开（公告）日：2007-09-13

  The present invention relates to a novel class of hydroxamic acid derivatives having a benzothiophene or thiophene backbone. The hydroxamic acid compounds can be used to treat cancer. The hydroxamic acid compounds can also inhibit historic deacetylase and are suitable for use in selectively inducing terminal differentiation, and arresting cell growth and/or apoptosis of neoplastic cells, thereby inhibiting proliferation of such cells. Thus, the compounds of the present invention are useful in treating a patient having a tumor characterized by proliferation of neoplastic cells. The compounds of the invention are also useful in the prevention and treatment of TRX-mediated diseases, such as autoimmune, allergic and inflammatory diseases, and in the prevention and/or treatment of diseases of the central nervous system (CNS), such as neurodegenerative diseases. The present invention further provides pharmaceutical compositions comprising the hydroxamic acid derivatives and safe dosing regimens of these pharmaceutical compositions, which are easy to follow, and which result in a therapeutically effective amount of the hydroxamic acid derivatives in vivo.

  本发明涉及一种新型的羟胺酸衍生物，其具有苯并噻吩或噻吩骨架。这些羟胺酸化合物可用于治疗癌症。这些羟胺酸化合物还可以抑制组蛋白去乙酰化酶，并适用于选择性诱导末端分化，阻止肿瘤细胞的生长和/或凋亡，从而抑制这些细胞的增殖。因此，本发明的化合物对于治疗具有肿瘤细胞增殖特征的患者是有用的。本发明的化合物还适用于预防和治疗TRX介导的疾病，例如自身免疫性、过敏性和炎症性疾病，以及预防和/或治疗中枢神经系统（CNS）疾病，例如神经退行性疾病。本发明还提供了包含羟胺酸衍生物的药物组合物和这些药物组合物的安全剂量方案，其易于遵循，并且在体内产生治疗有效量的羟胺酸衍生物。