2-iodohydroxyiminoacetanilide | 117500-16-0

• 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-iodohydroxyiminoacetanilide
• 英文别名: 2-Iod-α-isonitrosoacetanilid；2'-hydroxyimino-2-iodoacetanilide；hydroxyimino-acetic acid-(2-iodo-anilide)；Hydroxyimino-essigsaeure-(2-jod-anilid)；2-(hydroxyimino)-N-(2-iodophenyl)acetamide；2-hydroxyimino-N-(2-iodophenyl)acetamide
• CAS: 117500-16-0
• 化学式: C₈H₇IN₂O₂
• 分子量: 290.06
• InChiKey: QOSIKWJYKCKWNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-iodohydroxyiminoacetanilide 在 硫酸 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 生成 2-hydroxy-N'-(7-iodo-2-oxoindol-3-yl)benzohydrazide
  参考文献：
  名称：

  Chemical Synthesis, in Vitro Acetohydroxyacid Synthase (AHAS) Inhibition, Herbicidal Activity, and Computational Studies of Isatin Derivatives

  摘要：

  Acetohydroxyacid synthase (AHAS) catalyzes the first common step in the biosynthesis of the branched-chain amino adds. As a result of its metabolic importance in plants, it is a target for many commercial herbicides. Virtual screening analysis inspired the evaluation of 19 commercially available isatin analogues and 13 newly synthesized isatin derivatives as novel AFIAS inhibitors and for their herbicidal activity. The best compound demonstrated 95% inhibition of the activity of Arabidopsis thaliana AHAS at a concentration of 100 mg L-1, whereas the herbicidal activities of three compounds reached 50% inhibition at a concentration of 10 mg L-1 using the rape root growth test. CoMFA contour models were established to understand the structure-activity relationships for this class of AHAS inhibitor. The compounds were docked to the active site cavity of A. thaliana AHAS using FlexX, and the dominant binding mode was consistent with frontier molecular orbital from DFT calculations. This is the first comprehensive study of isatin derivatives as AHAs inhibitors and provides a valuable starting point for the design of new herbicides.

  DOI：

  10.1021/jf2021607
• 作为产物：
  描述：

  2,2,2-trichloro-N-(2-iodophenyl)acetamide 在 盐酸羟胺 作用下， 以 水 为溶剂， 反应 4.0h， 以18.53 g的产率得到2-iodohydroxyiminoacetanilide
  参考文献：
  名称：

  Chemical Synthesis, in Vitro Acetohydroxyacid Synthase (AHAS) Inhibition, Herbicidal Activity, and Computational Studies of Isatin Derivatives

  摘要：

  Acetohydroxyacid synthase (AHAS) catalyzes the first common step in the biosynthesis of the branched-chain amino adds. As a result of its metabolic importance in plants, it is a target for many commercial herbicides. Virtual screening analysis inspired the evaluation of 19 commercially available isatin analogues and 13 newly synthesized isatin derivatives as novel AFIAS inhibitors and for their herbicidal activity. The best compound demonstrated 95% inhibition of the activity of Arabidopsis thaliana AHAS at a concentration of 100 mg L-1, whereas the herbicidal activities of three compounds reached 50% inhibition at a concentration of 10 mg L-1 using the rape root growth test. CoMFA contour models were established to understand the structure-activity relationships for this class of AHAS inhibitor. The compounds were docked to the active site cavity of A. thaliana AHAS using FlexX, and the dominant binding mode was consistent with frontier molecular orbital from DFT calculations. This is the first comprehensive study of isatin derivatives as AHAs inhibitors and provides a valuable starting point for the design of new herbicides.

  DOI：

  10.1021/jf2021607

文献信息

• Methods and compositions for selectin inhibition
  申请人：Kaila Neelu

  公开号：US20050101568A1

  公开（公告）日：2005-05-12

  The present invention relates to the field of anti-inflammatory substances, and more particularly to novel compounds that act as antagonists of the mammalian adhesion proteins known as selectins. In some embodiments, methods for treating selectin mediated disorders are provided which include administration of compound of Formula I: wherein the constituent variables are defined herein.

  本发明涉及抗炎物质领域，更具体地涉及一种作为哺乳动物粘附蛋白选择素拮抗剂的新化合物。在某些实施例中，提供了治疗选择素介导的疾病的方法，包括给予式I化合物的治疗，其中其中组成变量在此定义。
• Methods and Compositions for Selectin Inhibition
  申请人：Kaila Neelu

  公开号：US20080255192A1

  公开（公告）日：2008-10-16

  The present teachings relate to novel compounds of formula I: wherein the constituent variables are as defined herein. Compounds of the present teachings can act as antagonists of the mammalian adhesion proteins known as selecting. Methods for treating or preventing selectin-mediated disorders are provided, which include administration of these compounds in a therapeutically effective amount.

  本发明涉及一种新的化合物，其化学式为I：其中组成变量如此处所定义。本发明的化合物可以作为哺乳动物粘附蛋白选择素的拮抗剂。提供了治疗或预防选择素介导的疾病的方法，其中包括以治疗有效剂量的方式给予这些化合物。
• DIHYDROOROTATE DEHYDROGENASE INHIBITORS
  申请人：Thunuguntla Siva Sanjeeva Rao

  公开号：US20120028959A1

  公开（公告）日：2012-02-02

  The invention relates to compounds of formula (I) wherein R 1 , R 2 , X 1 , X 2 , Y, R a , R b , Q have the meanings given in claim 1 . The compounds are useful e.g. in the treatment of autoimmune disorders, such as multiple sclerosis and also in the treatment of cancer disorders.

  本发明涉及式(I)的化合物，其中R1、R2、X1、X2、Y、Ra、Rb、Q的含义如权利要求书所述。该化合物在治疗自身免疫性疾病，如多发性硬化症，以及治疗癌症方面具有有用性。
• Dihydroorotate dehydrogenase inhibitors
  申请人：Thunuguntla Siva Sanjeeva Rao

  公开号：US09006454B2

  公开（公告）日：2015-04-14

  The invention relates to compounds of formula (I) wherein R1, R2, X1, X2, Y, Ra, Rb, Q have the meanings given in claim 1. The compounds are useful e.g. in the treatment of autoimmune disorders, such as multiple sclerosis and also in the treatment of cancer disorders.

  本发明涉及式（I）的化合物，其中R1，R2，X1，X2，Y，Ra，Rb，Q具有权利要求书1中给出的含义。这些化合物可用于治疗自身免疫性疾病，如多发性硬化症，也可用于治疗癌症等疾病。
• Synthesis and Antiproliferatory Activities Evaluation of Multi-Substituted Isatin Derivatives
  作者：Ying Ding、Lianbo Zhao、Ying Fu、Lei Hao、Yupeng Fu、Yuan Yuan、Peng Yu、Yuou Teng

  DOI：10.3390/molecules26010176

  日期：——

  reaction. The structures of these derivatives were confirmed by 1H-NMR, 13C-NMR, and HR-MS. Inhibition of proliferation activities of these derivatives against human leukemia cells (K562), human hepatocellular carcinoma cells (HepG2) and human colon carcinoma cells (HT-29) were evaluated in vitro using the MTT assay. Among the series, compound 4l exhibited strong antiproliferatory activities against K562,

  利用强大的桑德迈尔反应合成了一系列多取代靛红衍生物。这些衍生物的结构均通过1H-NMR、13C-NMR和HR-MS证实。使用MTT测定体外评估这些衍生物对人白血病细胞(K562)、人肝细胞癌细胞(HepG2)和人结肠癌细胞(HT-29)增殖活性的抑制作用。其中，化合物4l对K562、HepG2和HT-29细胞表现出较强的抗增殖活性，IC50值分别为1.75、3.20和4.17 μM。随后评价化合物4l在K562细胞中的形态学、生长抑制和凋亡作用、在HepG2细胞中的伤口愈合作用以及在HUVEC细胞的基质凝胶中的管形成作用。所有结果表明化合物4l可以作为进一步研究中潜在的抗肿瘤剂。