2-hydroxy-5-iodobenzohydrazide | 31822-04-5

• 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-hydroxy-5-iodobenzohydrazide
• CAS: 31822-04-5
• 化学式: C₇H₇IN₂O₂
• mdl: MFCD02380273
• 分子量: 278.049
• InChiKey: RVUJPMIELACRAY-UHFFFAOYSA-N

物化性质

• 密度：
  2.022±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxy-5-iodobenzohydrazide 、 对氯苯乙酮 以 乙醇 为溶剂， 反应 2.0h， 以85%的产率得到N'-[1-(4-chlorophenyl)ethylidene]-2-hydroxy-5-iodobenzohydrazide
  参考文献：
  名称：

  2-羟基-5-碘代苯甲酸中某些1,3,4-恶二唑啉衍生物的合成，结构和体外细胞毒性测试。

  摘要：

  描述了从水杨酸甲酯开始合成九种基于5碘水杨酸的1,3,4-恶二唑啉衍生物的新方法。这些化合物是2- [4-乙酰基-5-甲基-5-（3-硝基苯基）-4,5-二氢-1,3,4-恶二唑-2-基] -4-碘苯基乙酸酯（6a），2 -[4-乙酰基-5-甲基-5-（4-硝基苯基）-4,5-二氢-1,3,4-恶二唑-2-基] -4-乙酸碘苯酯（6b），2-（4-乙酰基-5-甲基-5-苯基-4,5-二氢-1,3,4-恶二唑-2-基）-4-碘代乙酸苯酯，C 19 H 17 IN 2 O 4（6c），2- [4 -乙酰基-5-（4-氟苯基）-5-甲基-4,5-二氢-1,3,4-恶二唑-2-基] -4-碘代乙酸苯酯，C 19 H 16 FIN 2 O 4（6d），2- [4-乙酰基-5-（4-氯苯基）-5-甲基-4,5-二氢-1,3,4-恶二唑-2-基] -4-乙酸碘苯酯，C 19 H 16 ClIN 2 O 4（6e），2-

  DOI：

  10.1107/s2053229618008719
• 作为产物：
  描述：

  5-碘水杨酸甲酯 在 肼 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以57%的产率得到2-hydroxy-5-iodobenzohydrazide
  参考文献：
  名称：

  作为抗糖尿病药的新的atranorin的N-取代酰肼衍生物的合成，α-葡萄糖苷酶抑制和分子对接研究。

  摘要：

  通过使具有天然depside结构（1）的化合物atranorin与一系列肼反应，可以合成一系列新型的N-取代的酰肼衍生物。天然产物和12个新的类似物（2 - 13）进行了调查抑制α葡糖苷酶。所述Ñ取代肼衍生物表现出更有效的抑制比原来的。通过对接分析证实了实验结果。这项研究表明这些化合物是用于糖尿病治疗的有前途的分子。使用化合物2进行了分子动力学模拟演示了在长达20 ns的仿真过程中使用Gromac的最佳对接模型，以探索复杂配体蛋白的稳定性。此外，所有合成的酶活性的化合物2 - 13针对正常细胞系HEK293，用于评估它们的细胞毒性，进行了评价。

  DOI：

  10.1016/j.bmcl.2020.127359

文献信息

• [EN] ANTI-BACTERIAL PYRUVATE KINASE MODULATOR COMPOUNDS, COMPOSITIONS, USES, AND METHODS<br/>[FR] COMPOSÉS ANTIBACTÉRIENS MODULATEURS DE LA PYRUVATE KINASE, COMPOSITIONS, UTILISATIONS ET MÉTHODES ASSOCIÉES
  申请人：UNIV BRITISH COLUMBIA

  公开号：WO2012051708A1

  公开（公告）日：2012-04-26

  Compounds having a structure of Formulas A-C are provided. Uses of such compounds as an antibiotic, including both gram-negative and gram-positive micro-organisms, as well as methods of treatment and uses involving such compounds are provided.

  提供了具有A-C式结构的化合物。提供了这些化合物作为抗生素的用途，包括革兰氏阴性和革兰氏阳性微生物，以及涉及这些化合物的治疗方法和用途。
• Optimization and structure–activity relationships of a series of potent inhibitors of methicillin-resistant Staphylococcus aureus (MRSA) pyruvate kinase as novel antimicrobial agents
  作者：Nag S. Kumar、Emily A. Amandoron、Artem Cherkasov、B. Brett Finlay、Huansheng Gong、Linda Jackson、Sukhbir Kaur、Tian Lian、Anne Moreau、Christophe Labrière、Neil E. Reiner、Raymond H. See、Natalie C. Strynadka、Lisa Thorson、Edwin W.Y. Wong、Liam Worrall、Roya Zoraghi、Robert N. Young

  DOI：10.1016/j.bmc.2012.10.002

  日期：2012.12

  A novel series of hydrazones were synthesized and evaluated as inhibitors of methicillin-resistant Staphylococcus aureus (MRSA) pyruvate kinase (PK). PK has been identified as one of the most highly connected 'hub proteins' in MRSA. PK has been shown to be critical for bacterial survival which makes it a potential target for development of novel antibiotics and the high degree of connectivity implies it should be very sensitive to mutations and thus less able to develop resistance. PK is not unique to bacteria and thus a critical requirement for such a PK inhibitor would be that it does not inhibit the homologous human enzyme(s) at therapeutic concentrations. Several MRSA PK inhibitors (including 8d) were identified using in silico screening combined with enzyme assays and were found to be selective for bacterial enzyme compared to four human PK isoforms (M1, M2, R and L). However these lead compounds did not show significant inhibitory activity for MRSA growth presumably due to poor bacterial cell penetration. Structure-activity relationship (SAR) studies were carried out on 8d and led us to discover more potent compounds with enzyme inhibiting activities in the low nanomolar range and some were found to effectively inhibit bacteria growth in culture with minimum inhibitory concentrations (MIC) as low as 1 mu g/mL. These inhibitors bind in two elongated flat clefts found at the minor interfaces in the homo-tetrameric enzyme complex and the observed SAR is in keeping with the size and electronic constraints of these binding sites. Access to the corresponding sites in the human enzyme is blocked. (C) 2012 Elsevier Ltd. All rights reserved.
• Design, modification of phyllanthone derivatives as anti-diabetic and cytotoxic agents
  作者：Ngoc-Hong Nguyen、Van-Giau Vo、Hoang-Vinh-Truong Phan、Thanh-The Ngo、Jirapast Sichaem、Thi-Phuong Nguyen、Huu-Hung Nguyen、Duc-Dung Pham、Tien-Cong Nguyen、Van-Kieu Nguyen、Thuc-Huy Duong

  DOI：10.1080/14786419.2020.1788023

  日期：2022.1.2

  Twelve benzylidene derivatives, one Baeyer-Villiger oxidative, six imine derivatives were successfully designed and synthesised from phyllanthone. In the search for potential new anti-diabetic agents, phyllanthone along with its benzylidene and oxidation analogues were evaluated for enzyme inhibition against alpha-glucosidase. In the benzylidene series, most analogues displayed stronger activity than the mother compound. Compound 1c revealed the strongest activity, outperforming the acarbose positive control with an IC50 value of 19.59 mu M. Phyllanthone and its derivatives were then tested for cytotoxic activity against the K562 cell line. The imine analogues displayed the most powerful cytotoxic activity with 3c and 3d having IC50 values of 57.55 and 68.02 mu M, respectively.[GRAPHICS].