2-cyano-N-(2-hydroxyphenyl)acetamide | 3815-12-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-cyano-N-(2-hydroxyphenyl)acetamide
• CAS: 3815-12-1
• 化学式: C₉H₈N₂O₂
• mdl: MFCD02323202
• 分子量: 176.175
• InChiKey: VPYDYCHWWHBLLR-UHFFFAOYSA-N

物化性质

• 熔点：
  200-201 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  439.0±30.0 °C(Predicted)
• 密度：
  1.346±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  73.1
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  2-cyano-N-(2-hydroxyphenyl)acetamide 在 盐酸羟胺 、 sodium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以53%的产率得到3-amino-3-(hydroxyimino)-N-[2-(hydroxyl)phenyl]propanamide
  参考文献：
  名称：

  Low Molecular Weight Amidoximes that Act as Potent Inhibitors of Lysine-Specific Demethylase 1

  摘要：

  The recently discovered enzyme lysine-specific demethylase 1 (LSD1) plays an important role in the epigenetic control of gene expression, and aberrant gene silencing secondary to LSD1 dysregulation is thought to contribute to the development of cancer. We reported that (bis)guanidines, (bis)biguanides, and their urea- and thiourea isosteres are potent inhibitors of LSD1 and induce the re-expression of aberrantly silenced tumor suppressor genes in tumor cells in vitro. We now report a series of small molecule amidoximes that are moderate inhibitors of recombinant LSD1 but that produce dramatic changes in methylation at the histone 3 lysine 4 (H3K4) chromatin mark, a specific target of LSD1, in Calu-6 lung carcinoma cells. In addition, these analogues increase cellular levels of secreted frizzle-related protein (SFRP) 2, H-cadherin (HCAD), and the transcription factor GATA4. These compounds represent leads for an important new series of drug-like epigenetic modulators with the potential for use as antitumor agents.

  DOI：

  10.1021/jm3002845
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 甲醇 、 盐酸羟胺 、 potassium acetate 作用下， 生成 2-cyano-N-(2-hydroxyphenyl)acetamide
  参考文献：
  名称：

  Borsche; Doeller, Justus Liebigs Annalen der Chemie, 1939, vol. 57, p. 53,57

  摘要：

  DOI：

文献信息

• Development of Novel AKR1C3 Inhibitors as New Potential Treatment for Castration-Resistant Prostate Cancer
  作者：Satoshi Endo、Hiroaki Oguri、Jin Segawa、Mina Kawai、Dawei Hu、Shuang Xia、Takuya Okada、Katsumasa Irie、Shinya Fujii、Hiroaki Gouda、Kazuhiro Iguchi、Takuo Matsukawa、Naohiro Fujimoto、Toshiyuki Nakayama、Naoki Toyooka、Toshiyuki Matsunaga、Akira Ikari

  DOI：10.1021/acs.jmedchem.0c00939

  日期：2020.9.24

  crystallographic study of AKR1C3 complexes with 2j and 2l. The inhibitors suppressed proliferation of prostate cancer 22Rv1 and PC3 cells through both androgen-dependent and androgen-independent mechanisms. Additionally, 2j and 2l prevented prostate tumor growth in a xenograft mouse model. Furthermore, the inhibitors significantly augmented apoptotic cell death induced by anti-CRPC drugs (abiraterone or enzalutamide)

  醛基酮还原酶（AKR）1C3催化活性雄激素的合成，从而促进前列腺癌的发展。AKR1C3还通过前列腺素和反应性醛的代谢促进非雄激素依赖性细胞增殖和存活。由于其在去势抵抗性前列腺癌（CRPC）组织中的升高，AKR1C3是CRPC的有希望的治疗靶标。在这项研究中，我们发现了一种新型的强效AKR1C3抑制剂N-（4-氟苯基）-8-羟基-2-亚氨基-2 H-色烯-3-羧酰胺（2d），并用IC 50合成了其衍生物值比其他AKR（1C1、1C2和1C4）高25-56 nM，选择性> 220倍。通过结晶研究AKR1C3与2j和2l的复合物阐明了抑制效力的结构因素。所述抑制剂通过雄激素依赖性和雄激素依赖性机制抑制前列腺癌22Rv1和PC3细胞的增殖。另外，2j和2l阻止了异种移植小鼠模型中前列腺肿瘤的生长。此外，这些抑制剂显着增加了由抗CRPC药物（阿比特龙或enzalutamide）诱导的凋亡细胞死亡。
• Synthesis of 8-hydroxy-2-iminochromene derivatives as selective and potent inhibitors of human carbonyl reductase 1
  作者：Dawei Hu、Namiki Miyagi、Yuki Arai、Hiroaki Oguri、Takeshi Miura、Toru Nishinaka、Tomoyuki Terada、Hiroaki Gouda、Ossama El-Kabbani、Shuang Xia、Naoki Toyooka、Akira Hara、Toshiyuki Matsunaga、Akira Ikari、Satoshi Endo

  DOI：10.1039/c5ob00847f

  日期：——

  Human carbonyl reductase 1 (CBR1), a member of the short-chain dehydrogenase/reductase superfamily, reduces anthracycline anticancer drugs to their less potent anticancer C-13 hydroxy metabolites, which are linked with pathogenesis of cardiotoxicity, a side effect of the drugs.

  人类羰基还原酶1（CBR1）是短链脱氢酶/还原酶超家族的成员，它将蒽环类抗癌药物还原为它们的较不具有抗癌作用的C-13羟基代谢物，这些代谢物与心脏毒性的发病机制相关，是这些药物的副作用之一。
• [EN] BENZOXAZOLE ACETONITRILES<br/>[FR] BENZOXAZOLE ACETONITRILES
  申请人：APPLIED RESEARCH SYSTEMS

  公开号：WO2005026159A1

  公开（公告）日：2005-03-24

  The present invention is related to benzoxazole acetonitriles as well as to pharmaceutical formulations containing such benzoxazole acetonitriles pof formula (I). Said benzoxazole acetonitriles are useful in the treatment of metabolic disorders mediated by insulin resistance or hyperglycernia, comprising diabetes type II, inadequate glucose tolerance, insulin resistance, obesity, polycystic ovary syndrome (PCOS). The present invention is furthermore related to methods of preparing benzoxazole acetonitriles (I). A is a pyrimidinyl.L is a secondary or tertiary amino group, or a 3-8 membered heterocycloalkyl, containing at least one heteroatom. selected from N, O, S or L is an acylarnino moiety.R1 is selected from the group comprising or consisting of hydrogen, sulfonyl, amino, CiC6-alkYl, C2-C6-alkenYl, C2-C6-alkynyl or Cl-C6-alkoxy, aryl, halogen, carboxy,aminocarbonyl, cyano or hydroxy.

  本发明涉及苯并噁唑乙腈，以及含有该苯并噁唑乙腈的药物配方（I）的制备方法。所述苯并噁唑乙腈在治疗由胰岛素抵抗或高甘油三酯引起的代谢紊乱方面具有用途，包括糖尿病II型、葡萄糖耐量不佳、胰岛素抵抗、肥胖、多囊卵巢综合征（PCOS）。A是嘧啶基。L是次级或三级氨基团，或者是含有至少一个来自N、O、S的杂原子的3-8环杂环烷基。R1选择自氢、磺酰基、氨基、CiC6-烷基、C2-C6-烯基、C2-C6-炔基、Cl-C6-烷氧基、芳基、卤素、羧基、氨基羰基、氰基或羟基。
• Interaction of 3,8-Disubstituted Imidazo-[5,1-C][1,2,4]Triazines with Nucleophiles**
  作者：E. V. Sadchikova、V. S. Mokrushin*

  DOI：10.1007/s10593-014-1557-5

  日期：2014.10

  4-aminoimidazo[5,1-с][1,2,4]triazine-3,8-dicarboxylate in reactions with nucleophiles and demonstrated the possibility of selective formation of monoamides by interaction with primary and secondary aliphatic amines. It was determined that the carbon atom at position 4 of imidazo[1,5-с][1,2,4]triazine system underwent nucleophilic attack, enabling the synthesis of imidazo-[1',5':3,4][1,2,4]triazino[5,6-b][1

  我们研究了4-氨基咪唑并[5,1-с] [1,2,4]三嗪-3,8-二羧酸二乙酯在与亲核试剂反应中的反应性，并证明了通过与伯和仲脂族相互作用选择性形成单酰胺的可能性胺类。已确定咪唑[1,5-с] [1,2,4]三嗪系统第4位的碳原子受到亲核攻击，从而能够合成咪唑-[1'，5'：3,4] [ 1,2,4]三嗪并[5,6-b] [1,5]苯并x氮平和咪唑并[1'，5'：3,4] [1,2,4]三嗪并[5,6-b] [1 ，5]-苯二氮卓类以及（吡唑-4-亚甲基肼基）咪唑，具体取决于所使用的双亲核试剂。
• Destruction and Construction: Application of Dearomatization Strategy in Aromatic Carbon-Nitrogen Bond Functionalization
  作者：Shuo-En Wang、Linfei Wang、Qiuqin He、Renhua Fan

  DOI：10.1002/anie.201508161

  日期：2015.11.9

  formation of carbon–carbon bonds through the functionalization of aromatic carbon–nitrogen bonds is a highly attractive synthetic strategy in the synthesis of aromatic molecules. In this paper, we report a novel aromatic carbon–nitrogen bond functionalization reaction by using a simple dearomatization strategy. Through this process para‐substituted anilines serve as a potential aryl source in the construction

  通过芳族碳-氮键的官能化形成碳-碳键是合成芳族分子中极富吸引力的合成策略。在本文中，我们通过使用简单的脱芳构化策略报告了一种新型的芳族碳-氮键官能化反应。通过此过程，对位取代的苯胺可作为潜在的芳基来源，用于构建一系列功能化的芳族分子，例如季碳中心，α-酮酸酯和醛。