N-hydroxy-2-(pyridin-2-yl)acetamide | 83421-34-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-hydroxy-2-(pyridin-2-yl)acetamide
• 英文别名: N-hydroxy-(pyridin-2-yl)acetamide；N-hydroxy-2-pyridineacetamide；N-hydroxy-2-pyridin-2-ylacetamide
• CAS: 83421-34-5
• 化学式: C₇H₈N₂O₂
• 分子量: 152.153
• InChiKey: JVXKBGDLLACBGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-hydroxy-2-(pyridin-2-yl)acetamide 、 7β-<2-(2-aminothiazol-4yl)-2-(Z)-methoximinoacetamide>-3-iodomethyl-2-<(trimethylsilyloxy)carbonyl>cephalosporin 在 甲醇 作用下， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of a series of parenteral 3'-quaternary ammonium cephalosporins

  摘要：

  The preparation and biological evaluation of a series of 7 beta-[2-(2-aminothiazol-4-yl)-2(Z)-methoximinoacetamido]cep halosporins, substituted at the 3'-position with monocyclic or bicyclic nitrogen-containing heterocycles are described. The resulting family of parenteral compounds displays a broad spectrum of antibacterial activity. Some compounds exhibit a similar level of Gram-negative activity to that of the "third-generation" cephalosporins with increased staphylococcal activity. The in vitro and in vivo antimicrobial activity, structure-activity relationships, beta-lactamase stability, and in vitro and in vivo pharmacological evaluations are presented.

  DOI：

  10.1021/jm00170a011
• 作为产物：
  描述：

  2-吡啶乙酸乙酯 在 盐酸羟胺 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 以50%的产率得到N-hydroxy-2-(pyridin-2-yl)acetamide
  参考文献：
  名称：

  理解[4 + 2]环加成中酰基亚硝基化合物反应的实验和计算方法

  摘要：

  在甲醇中使用CuCl 2和2-乙基-2-恶唑啉催化好氧氧化苯基羟基氨基甲酸酯1和1-羟基-3-苯基脲2得到原位的酰基亚硝基物质，将其捕获在亚硝基-Diels-Alder（NDA）反应中。各种二烯以高产率（90-98％）提供相应的环加合物。竞争烯产品也存在于含有烯烃的π键和烯丙基σ-键二烯，和烯产率更高的1比2。手性异羟肟酸（R）-1-羟基-3-（1-苯基乙基脲）3的用途（在相同条件下）以高收率（97-99％）得到了NDA环加合物，没有2,3-二甲基-1,3-丁二烯的烯烃产物。从其他异羟肟酸类似物[RCONHOH（R ​​= PhCH 2 4 ; Ph（CH 2）2 5 ; Ph（CH 2）3 6 ; Ph（CH 2）4 7 ; Ph 8 ; 2-吡啶基9 ; 3-吡啶基10使用高碘酸钠获得]用铜-氧化各种二烯而是导致从异羟肟酸可变NDA的产率（13-51％）1 - 10具有环己-1,3-二烯和2

  DOI：

  10.1021/acs.joc.5b01470

文献信息

• Cephalosporin antibiotics
  申请人：Eli Lilly and Company

  公开号：US04336253A1

  公开（公告）日：1982-06-22

  Cephalosporin antibiotics represented by the formula ##STR1## wherein R is hydrogen, C.sub.1 -C.sub.4 alkyl or a carboxy substituted alkyl group; R.sub.1 is H or C.sub.1 -C.sub.4 alkyl; n is 0, 1 or 2; and A and A' independently are hydrogen, C.sub.1 -C.sub.4 alkyl or allyl; and pharmaceutically acceptable salts thereof are broad spectrum antibiotics useful in the treatment of gram positive and gram negative infections of mammals.

  头孢菌素抗生素由以下公式代表##STR1##其中R为氢、C.sub.1-C.sub.4烷基或一个羧基取代的烷基基团；R.sub.1为H或C.sub.1-C.sub.4烷基；n为0、1或2；A和A'独立地为氢、C.sub.1-C.sub.4烷基或烯丙基；以及它们的药用盐是用于治疗哺乳动物的革兰氏阳性和革兰氏阴性感染的广谱抗生素。
• Inhibition of 1-Deoxy-<scp>d</scp>-Xylulose-5-Phosphate Reductoisomerase by Lipophilic Phosphonates: SAR, QSAR, and Crystallographic Studies
  作者：Lisheng Deng、Jiasheng Diao、Pinhong Chen、Venugopal Pujari、Yuan Yao、Gang Cheng、Dean C. Crick、B. V. Venkataram Prasad、Yongcheng Song

  DOI：10.1021/jm200363d

  日期：2011.7.14

  1-Deoxy-D-xylulose-5-phosphate reductoisomerase (DXR) is a novel target for developing new antibacterial (including antituberculosis) and antimalaria drugs. Forty-one lipophilic phosphonates, representing a new class of DXR inhibitors, were synthesized, among which 5-phenylpyridin-2-ylmethylphosphonic acid possesses the most activity against E. coli DXR (EcDXR) with a K-i of 420 nM. Structure-activity relationships (SAR) are discussed, which can be rationalized using our EcDXR:inhibitor structures, and a predictive quantitative SAR (QSAR) model is also developed. Since inhibition studies of DXR from Mycobacterium tuberculosis (MtDXR) have not been performed well, 48 EcDXR inhibitors with a broad chemical diversity were found, however, to generally exhibit considerably reduced activity against MtDXR. The crystal structure of a, MtDXR:inhibitor complex reveals the flexible loop containing the residues 198-208 has no strong interactions with the 3,4-dichlorophenyl group of the inhibitor, representing a structural basis for the reduced activity. Overall, these results provide implications in the future design and development of potent DXR inhibitors.
• Efficient Continuous Flow Synthesis of Hydroxamic Acids and Suberoylanilide Hydroxamic Acid Preparation
  作者：Elena Riva、Stefania Gagliardi、Caterina Mazzoni、Daniele Passarella、Anna Rencurosi、Daniele Vigo、Marisa Martinelli

  DOI：10.1021/jo900144h

  日期：2009.5.1

  A continuous flow tubing reactor can be used to readily transform methyl or ethyl carboxylic esters into the corresponding hydroxamic acids. Flow rate, reactor volume, and temperature were optimized for the preparation of a small collection of hydroxamic acids. Synthetic advantages were identified as an increased reaction rate and higher product purity. This method was also successfully applied to the multistep preparation of suberoylanilide hydroxamic acid, a potent HDAC inhibitor used in anticancer therapy.
• BROWN, RAYMOND F.;KINNICK, MICHAEL D.;MORIN, JOHN M. (JR);VASILEFF, ROBER+, J. MED. CHEM., 33,(1990) N, C. 2114-2121
  作者：BROWN, RAYMOND F.、KINNICK, MICHAEL D.、MORIN, JOHN M. (JR)、VASILEFF, ROBER+

  DOI：——

  日期：——
• US4336253A
  申请人：——

  公开号：US4336253A

  公开（公告）日：1982-06-22