6,8-diiodocoumarin-3-carboxylic acid | 98994-72-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 6,8-diiodocoumarin-3-carboxylic acid
• 英文别名: 6,8-diiodo-2-oxo-2H-chromene-3-carboxylic acid；UBP658；6,8-diICcaH；6,8-Dijod-2-oxo-2H-chromen-3-carbonsaeure；6,8-diiodo-2-oxochromene-3-carboxylic acid
• CAS: 98994-72-0
• 化学式: C₁₀H₄I₂O₄
• 分子量: 441.948
• InChiKey: CMBVBZQPXISBGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,8-diiodocoumarin-3-carboxylic acid 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 1.0h， 以92%的产率得到6,8-diiodocoumarin-3-carbonyl chloride
  参考文献：
  名称：

  Synthesis and characterization of new diiodocoumarin derivatives with promising antimicrobial activities

  摘要：

  制备了一系列6,8-二碘香豆素-3-N-羧酰胺（4-11）。将乙酸乙酯的6,8-二碘香豆素-3-羧酸乙酯（1）与乙酰氰/ NH4OAc处理后，得到乙酸2-（3-羧酰胺-6,8-二碘香豆素-4-基）-2-乙腈酸乙酯（12）和2-氨基-4-羟基-7,9-二碘香豆酮[3,4-c]吡啶-1-碳腈（13），并在NH4OAc或甲胺的存在下用丙酮处理后，得到乙酸4-氧代-2,6-甲烷基-2-甲基-3,4,5,6-四氢-8,10-二碘苯并[2,1-g]-2H-1,3-噁唑啉-5-羧酸乙酯衍生物14a,b。所有化合物均评估了其抗微生物活性，化合物12-14a,b对所有测试的微生物均表现出明显的效果。

  DOI：

  10.3762/bjoc.7.199
• 作为产物：
  描述：

  ethyl 6,8-diiodo-2-oxo-2H-chromene-3-carboxylate 在 lithium hydroxide monohydrate 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 生成 6,8-diiodocoumarin-3-carboxylic acid
  参考文献：
  名称：

  3-羰基，3-酰基和3-羧基肼基香豆素衍生物的合成和选择性人单胺氧化酶抑制作用

  摘要：

  几个-3-羰基（1 - 26），3-酰基（27 - 52），和3- carboxyhydrazido（53 - 58）香豆素已经以高收率（72-99％）合成并测试在体外对它们的人类单胺氧化酶A和B（hMAO-A和hMAO-B）的抑制活性。评价了香豆素核上的不同取代基对生物活性和同工型选择性的影响。对于使用IC 50获得高效且选择性的hMAO-B抑制剂而言，在3-乙酯香豆素环的C7位取代或在C3引入肼基取代基很重要。值在纳摩尔范围内。一些衍生物也进行了稳定性测试，在体外没有化​​学裂解。

  DOI：

  10.1016/j.ejmech.2011.07.017

文献信息

• Solid phase synthesis of substituted coumarin-3-carboxylic acids via the Knoevenagel condensation
  作者：Brett T Watson、Gerda E Christiansen

  DOI：10.1016/s0040-4039(98)01255-6

  日期：1998.8

  A solid phase synthesis of substituted coumarin-3-carboxylates using the Knoevenagel condensation reaction between ethyl malonate bound to the Wang resin and ortho-hydroxyarylaldehydes is described. The reaction has been shown to proceed cleanly to give the desired products.

  描述了使用结合在Wang树脂上的丙二酸乙酯和邻-羟基芳基醛之间的Knoevenagel缩合反应固相合成取代的香豆素-3-羧酸酯。已显示该反应可干净进行，得到所需产物。
• Synthesis and Antiproliferative Effect of Halogenated Coumarin Derivatives
  作者：Tinuccia Dettori、Giuseppina Sanna、Andrea Cocco、Gabriele Serreli、Monica Deiana、Vanessa Palmas、Valentina Onnis、Luca Pilia、Nicola Melis、Davide Moi、Paola Caria、Francesco Secci

  DOI：10.3390/molecules27248897

  日期：——

  performed. Among the screened compounds, coumarins 6,8-dibromo-2-oxo-2H-chromene-3-carbonitrile 2h and 6,8-diiodo-2-oxo-2H-chromene-3-carbonitrile 2k exhibited the most antiproliferative effect in thyroid cancer-derived cells TPC-1. The apoptosis assay showed that both 2h and 2k induced apoptosis in TPC-1 thyroid cancer cells. According to these experiments, both coumarins induced a slight increase in TPC-1

  已经研究了一系列 6- 和 6,8- 卤代香豆素衍生物作为针对一组肿瘤和正常细胞系的潜在抗增殖化合物。通过MTT方法测定细胞毒性作用。为了研究细胞毒性作用中涉及的潜在分子机制，进行了细胞凋亡测定、细胞周期分析、活性氧 (ROS) 和还原型谷胱甘肽分析。在筛选的化合物中，香豆素 6,8-dibromo-2-oxo-2H-chromene-3-carbonitrile 2h 和 6,8-diiodo-2-oxo-2H-chromene-3-carbonitrile 2k 在甲状腺中表现出最强的抗增殖作用癌细胞 TPC-1。细胞凋亡测定显示 2h 和 2k 均诱导 TPC-1 甲状腺癌细胞的细胞凋亡。根据这些实验，两种香豆素均诱导 G2/M 期 TPC-1 细胞的轻微增加和 S 期的减少。在用二碘香豆素 2k 处理的 TPC-1 中观察到 ROS 水平显着增加，而二溴香豆素 2h 以剂量和时间依赖性方式诱导
• Benzopyran compound and use of the same
  申请人：MITSUI TOATSU CHEMICALS, Inc.

  公开号：EP0635504A1

  公开（公告）日：1995-01-25

  The invention is a 2H-1-benzopyran-2-on compound represented by the formula (1) : and a colorless ultraviolet absorber consisting of the compound, and a thermoplastic resin composition and formed article comprising said ultraviolet absorber, and can provide a thermoplastic resin composition and a formed article of the composition which have excellent heat stability and sublimation resistance, comprise a non-coloring ultraviolet absorber, and are excellent in ultraviolet barrier property.

  本发明是一种由式（1）表示的 2H-1-苯并吡喃-2-酮化合物： 和由该化合物组成的无色紫外线吸收剂，以及包含所述紫外线吸收剂的热塑性树脂组合物和成型品，可提供热稳定性和抗升华性优异、包含无色紫外线吸收剂、紫外线阻隔性优异的热塑性树脂组合物和由该组合物制成的成型品。
• Synthesis of Coumarin-3-O-acylisoureas by Different Carbodiimides
  作者：Leonardo Bonsignore、Filippo Cottiglia、Silvio M. Lavagna、Giuseppe Loy、Daniela Secci

  DOI：10.3987/com-98-s(h)18

  日期：——

  The synthesis and isolation of some O-acylisourea derivatives are described. The reaction between coumarin-3-carboxylic acids and diisopropyl- and di-tert-butyl-carbodiimides leads only to coumarin-isourea derivatives except for two reactions which lead, as by-products, also to coumarin-urea derivatives.
• Coumarin-3-carboxylic acid derivatives as potentiators and inhibitors of recombinant and native N-methyl-d-aspartate receptors
  作者：Mark W. Irvine、Blaise M. Costa、Arturas Volianskis、Guangyu Fang、Laura Ceolin、Graham L. Collingridge、Daniel T. Monaghan、David E. Jane

  DOI：10.1016/j.neuint.2011.12.020

  日期：2012.9

  N-Methyl-D-aspartate receptors (NMDARs) are known to be involved in a range of neurological and neurodegenerative disorders and consequently the development of compounds that modulate the function of these receptors has been the subject of intense interest. We have recently reported that 6-bromocoumarin-3-carboxylic acid (UBP608) is a negative allosteric modulator with weak selectivity for GluN2A-containing NMDARs. In the present study, a series of commercially available and newly synthesized coumarin derivatives have been evaluated in a structure-activity relationship (SAR) study as modulators of recombinant NMDAR activity. The main conclusions from this SAR study were that substituents as large as iodo were accommodated at the 6-position and that 6,8-dibromo or 6,8-diiodo substitution of the coumarin ring enhanced the inhibitory activity at NMDARs. These coumarin derivatives are therefore excellent starting points for the development of more potent and GluN2 subunit selective inhibitors, which may have application in the treatment of a range of neurological disorders such as neuropathic pain, epilepsy and depression. Surprisingly, 4-methyl substitution of UBP608 to give UBP714, led to conversion of the inhibitory activity of UBP608 into potentiating activity at recombinant GluN1/GluN2 receptors. UBP714 also enhanced NMDAR mediated field EPSPs in the CA1 region of the hippocampus. UBP714 is therefore a novel template for the development of potent and subunit selective NMDAR potentiators that may have therapeutic applicability in the treatment of patients with cognitive deficits or schizophrenia. (C) 2012 Elsevier Ltd. All rights reserved.