2-(4-甲酰基苯氧基)-N-噻唑-2-基-乙酰胺 | 215503-93-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-(4-甲酰基苯氧基)-N-噻唑-2-基-乙酰胺
• 英文名称: 2-(4-formylphenoxy)-N-1,3-thiazol-2-ylacetamide
• 英文别名: 2-(4-formylphenoxy)-N-(thiazol-2-yl)acetamide；2-(4-formylphenoxy)-N-(1,3-thiazol-2-yl)acetamide
• CAS: 215503-93-8
• 化学式: C₁₂H₁₀N₂O₃S
• mdl: MFCD08575597
• 分子量: 262.289
• InChiKey: MXGHVNKPNQEZPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  96.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-甲酰基苯氧基)-N-噻唑-2-基-乙酰胺 在 ammonium acetate 、 溶剂黄146 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 2-{4-[2-amino-6-(4-chlorophenyl)-3-cyanopyrid-4-yl]phenoxy}-N-(thiazol-2-yl)acetamide
  参考文献：
  名称：

  Synthesis of New Thiazole-Pyridine Hybrids and Their Anticancer Activity

  摘要：

  A series of new thiazole incorporated pyridine derivatives containing the phenoxyacetamide moiety as a linking bridge has been synthesized. The synthetic strategy involves condensation of 2-(4-formylphenoxy)-N-(thiazol-2-yl)acetamide with cyanoacetic hydrazide followed by heterocyclization with acetylacetone, treatment of the produced acrylamides with malononitrile and substituted acetophenones, then heating the generated chalcones with mononitrile in acetic acid and ammonium acetate. In vitro anticancer activity of the newly synthesized thiazole-pyridine hybrids has been evaluated against prostate (PC3), liver (HepG2), laryngeal (Hep-2), and breast (MCF-7) cancer cell lines. One of thiazole-pyridine compounds 8c demonstrates higher activity (IC50 5.71 mu M) against breast cancer than 5-fluorouracil used as a reference (IC50 6.14 mu M). Molecular docking procedure has provided valuable information on the binding sites of the synthesized compounds with rho-associated protein kinase 1 (ROCK-1).

  DOI：

  10.1134/s1070363220100254
• 作为产物：
  描述：

  2-(2-氯乙酰胺基)噻唑 、 对羟基苯甲醛 在 sodium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以66%的产率得到2-(4-甲酰基苯氧基)-N-噻唑-2-基-乙酰胺
  参考文献：
  名称：

  Synthesis of New Thiazole-Pyridine Hybrids and Their Anticancer Activity

  摘要：

  A series of new thiazole incorporated pyridine derivatives containing the phenoxyacetamide moiety as a linking bridge has been synthesized. The synthetic strategy involves condensation of 2-(4-formylphenoxy)-N-(thiazol-2-yl)acetamide with cyanoacetic hydrazide followed by heterocyclization with acetylacetone, treatment of the produced acrylamides with malononitrile and substituted acetophenones, then heating the generated chalcones with mononitrile in acetic acid and ammonium acetate. In vitro anticancer activity of the newly synthesized thiazole-pyridine hybrids has been evaluated against prostate (PC3), liver (HepG2), laryngeal (Hep-2), and breast (MCF-7) cancer cell lines. One of thiazole-pyridine compounds 8c demonstrates higher activity (IC50 5.71 mu M) against breast cancer than 5-fluorouracil used as a reference (IC50 6.14 mu M). Molecular docking procedure has provided valuable information on the binding sites of the synthesized compounds with rho-associated protein kinase 1 (ROCK-1).

  DOI：

  10.1134/s1070363220100254

文献信息

• Parallel Solution-Phase Synthesis and General Biological Activity of a Uridine Antibiotic Analog Library
  作者：Omar Moukha-chafiq、Robert C. Reynolds

  DOI：10.1021/co4001452

  日期：2014.5.12

  coupling of the amino terminus of d-phenylalanine methyl ester to the free 5′-carboxylic acid moiety of 33 followed by sodium hydroxide treatment led to carboxylic acid analog 77. Hydrolysis of this material gave analog 78. The intermediate 77 served as the precursor for the preparation of novel dipeptidyl uridine analogs 79–99 through peptide coupling reactions to diverse amine reactants. None of the described

  在 NIH 路线图计划的中试规模库 (PSL) 计划下，以溶液相方式从胺2和羧酸33和77合成了一个包含 94 种尿苷抗生素类似物的小型库。多样醛，磺酰氯，和羧酸反应物套缩合，2，酸介导的水解导致后，向目标化合物3 - 32以良好的收率和高的纯度。同样，用不同的胺和磺胺处理33得到34 – 75。d氨基末端的偶联-苯丙氨酸甲酯到33的游离 5'-羧酸部分，然后用氢氧化钠处理产生羧酸类似物77。该材料的水解得到类似物78。中间77担任该前体为二肽基新颖尿苷类似物的制备79 - 99通过肽偶联到不同的胺反应剂反应。所描述的化合物均未显示出显着的抗癌或抗疟活性。通过 NIH MLPCN 计划提供和报告的初级筛选中的酶和受体，许多样品表现出各种有希望的抑制性、激动剂、拮抗剂或激活剂特性。
• Parallel Solution Phase Synthesis and Preliminary Biological Activity of a 5′-Substituted Cytidine Analog Library
  作者：Omar Moukha-Chafiq、Robert C. Reynolds、Jacob C. Wilson、Timothy S. Snowden

  DOI：10.1021/acscombsci.9b00072

  日期：2019.9.9

  NIH Roadmap Initiative and the Pilot Scale Library (PSL) Program. Reaction core compounds contained -NH2 (2) and -COOH (44 and 93) groups that were coupled to a diversity of reactants in a parallel, solution phase format to produce the target library. The assorted reactants included -NH2, -CHO, -SO2Cl, and -COOH functional groups, and condensation with the intermediate core materials 2 and 44 followed

  通过美国国立卫生研究院路线图计划和中试规模库（PSL）计划的资助，合成了一个由109个成员组成的5'-取代胞苷类似物库。反应核心化合物包含-NH2（2）和-COOH（44和93）基团，这些基团以平行溶液相的形式与多种反应物偶联，生成目标库。所分类的反应物包括-NH 2，-CHO，-SO 2 Cl和-COOH官能团，并且与中间核材料2和44缩合，然后进行酸性水解，以良好的产率和高纯度产生了3-91。d-苯丙氨酸甲酯的氨基末端与44和NaOH处理的游离5'-COOH的连接产生了核心库-COOH前体93。化合物93是我们独特的二肽基胞苷类似物94-114文库的重要组成部分，它通过-COOH基团与众多商业胺的酰胺偶联，然后进行酸性脱保护作用。通过MLPCN程序对完整的最终文库进行的初步筛选显示，在不同的生物学过程中命中数不多。这些命中可以被认为是命中率领先的优化和开发研究的起点。
• [EN] 2-PHENYL-3H-IMIDAZO[4,5-B]PYRIDINE DERIVATES USEFUL AS INHIBITORS OF MAMMALIAN TYROSINE KINASE ROR1 ACTIVITY<br/>[FR] DÉRIVÉS DE 2-PHÉNYL-3H-IMIDAZO[4,5-B]PYRIDINE UTILISÉS COMME INHIBITEURS DE L'ACTIVITÉ DE LA TYROSINE KINASE DE MAMMIFÈRE ROR1
  申请人：KANCERA AB

  公开号：WO2016124553A1

  公开（公告）日：2016-08-11

  A compound of formula (I´) or (I´´) or a pharmaceutically acceptable salt thereof. The compound is an inhibitor of mammalian kinase enzyme activity, including ROR1 tyrosine kinase activity and may be used in the treatment of disorders associated with such activity.

  化合物的化学式（I´）或（I´´）或其药学上可接受的盐。该化合物是哺乳动物激酶酶活性的抑制剂，包括ROR1酪氨酸激酶活性，并可用于治疗与该活性相关的疾病。
• Bi-functional complexes and methods for making and using such complexes
  申请人：Gouliaev Alex Haahr

  公开号：US11225655B2

  公开（公告）日：2022-01-18

  The present invention is directed to a method for the synthesis of a bi-functional complex comprising a molecule part and an identifier oligonucleotide part identifying the molecule part. A part of the synthesis method according to the present invention is preferably conducted in one or more organic solvents when a nascent bi-functional complex comprising an optionally protected tag or oligonucleotide identifier is linked to a solid support, and another part of the synthesis method is preferably conducted under conditions suitable for enzymatic addition of an oligonucleotide tag to a nascent bi-functional complex in solution.

  本发明涉及一种合成双功能复合物的方法，该复合物包括分子部分和识别分子部分的识别寡核苷酸部分。根据本发明的合成方法的一部分优选在一种或多种有机溶剂中进行，此时包含可选保护标签或寡核苷酸标识符的新生双功能复合物与固体支持物相连接，合成方法的另一部分优选在适合于将寡核苷酸标签酶加到溶液中的新生双功能复合物的条件下进行。
• Parallel Solution-Phase Synthesis of an Adenosine Antibiotic Analog Library
  作者：Omar Moukha-chafiq、Robert C. Reynolds

  DOI：10.1021/co300127z

  日期：2013.3.11

  A library of eighty one adenosine antibiotic analogs was prepared under the Pilot Scale Library Program of the NIH Roadmap initiative from 5'-amino-5'-deoxy-2',3'-O-isopropylidene-adenosine 3. Diverse aldehyde, sulfonyl chloride and carboxylic acid reactant sets were condensed to 3, in solution-phase fashion, leading after acid-mediated hydrolysis to the targeted compounds in good yields and high purity. No marked antituberculosis or anticancer activity was noted on preliminary cellular testing, but these nucleoside analogs should be useful candidates for other types of biological activity.