7-azido-4-methylcoumarin

• 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: 7-azido-4-methylcoumarin
• 英文别名: 7-azido-4-methyl-2H-chromen-2-one；7-azido-4-methyl-chromen-2-one；7-azido-4-methylchromen-2-one
• 化学式: C₁₀H₇N₃O₂
• 分子量: 201.184
• InChiKey: HEKDKVLIMUWRRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-azido-4-methylcoumarin 在 硫化氢 作用下， 生成 7-氨基-4-甲基香豆素
  参考文献：
  名称：

  [4Fe-4S] 模型簇的硫醇依赖性 NO 反应性和 Roussin 黑阴离子生成 H2S

  摘要：

  铁硫簇 (Fe-S) 已被确定为生物系统中一氧化氮 (NO) 的靶标。作为蛋白质结合研究的补充，合成模型提供了一个平台来研究根据受控反应环境产生哪些铁亚硝基化产物和副产物。我们之前展示了一个模型 [2Fe-2S] 系统，在硫醇存在下，该系统在亚硝基化时与另一种重要的气体递质硫化氢 (H 2 S) 一起产生二亚硝基铁络合物 (DNIC)，并假设与[4Fe-4S]簇在生物和合成系统中很大程度上产生了不一致的反应产物。 Roussin 黑阴离子 (RBA) [Fe 4 (μ 3 -S) 3 (NO) 7 ] −是先前建立的合成 [4Fe-4S] 簇与 NO 的反应产物。在这里，我们提出了在硫醇和硫醇盐存在下合成[4Fe-4S]簇亚硝基化的新反应性。 [Et 4 N] 2 [Fe 4 S 4 (SPh) 4 ] ( 1 ) 在过量 PhSH 存在下被亚硝基化，生成 H 2 S 和“RBA 样”中间体，当进一步与

  DOI：

  10.1021/acs.inorgchem.1c01328
• 作为产物：
  描述：

  (3-羟基-苯基)-氨基甲酸乙酯 在 盐酸 、 硫酸 、 溶剂黄146 、 sodium nitrite 作用下， 生成 7-azido-4-methylcoumarin
  参考文献：
  名称：

  Design, synthesis, cytotoxicity and mechanism of novel dihydroartemisinin-coumarin hybrids as potential anti-cancer agents

  摘要：

  To develop novel agents with anticancer activities, thirty-four new dihydroartemisinin-coumarin hybrids were designed and synthesized in this study. Those compounds were identified that had great anticancer activity against two cancer cell lines (MDA-MB-231 and HT-29). The structure-activity relationships of the derivatives were also discussed, and the results of docking analysis had shown that carbonic anhydrases IX (CA IX) was very likely to be one of the drug targets of the hybrids. Meanwhile, to clarify the mechanism of the anticancer activity of the hybrids molecule, we did further exploration in the bioactivity of the hybrids. The results had shown that these derivatives obviously inhibited proliferation of HT-29 cell lines, arrested G(0)/G(1) phase of HT-29 cells, suppressed the migration of tumor cells, and induced a great decrease in mitochondrial membrane potential leading to apoptosis of cancer cells. Interestingly, the hybrids also induced the other cell death pathway-ferroptosis. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.04.005

文献信息

• Organophosphorus-Catalysed Staudinger Reduction
  作者：Henri A. van Kalkeren、Jorick J. Bruins、Floris P. J. T. Rutjes、Floris L. van Delft

  DOI：10.1002/adsc.201100967

  日期：2012.5.21

  The first Staudinger reduction that is catalytic in phosphine has been developed, showing excellent yields and functional group selectivity. To this end we utilised dibenzophosphole catalysts and mild in situ reduction of the intermediate iminophosphoranes. We could avoid the necessity of water during the reduction, obtained no phosphine oxides as waste and thus enabled facile purification of the product

  已开发出在膦中具有催化作用的第一个Staudinger还原剂，显示出优异的收率和官能团选择性。为此目的，我们使用了二苯并磷催化剂和中间亚氨基正膦的适度原位还原。我们可以避免在还原过程中需要水，没有浪费任何氧化膦，因此可以轻松纯化产物。一系列叠氮化物以良好到极好的收率和高官能团耐受性被转化为胺。
• [EN] BORONATE-MEDIATED DELIVERY OF MOLECULES INTO CELLS<br/>[FR] ADMINISTRATION DE MÉDICAMENT MÉDIÉE PAR LES BORONATE
  申请人：WISCONSIN ALUMNI RES FOUND

  公开号：WO2013110005A1

  公开（公告）日：2013-07-25

  Methods for enhancing cellular uptake of cargo molecules by boronating the cargo molecule, particularly with one or more phenylboronic acid groups. Cellular uptake includes at least partial uptake into the cytosol. Boronation includes ligating, crosslinking or otherwise bonding one or more phenylboronic acids substituted to contain a reactive group to a cargo molecule. Boronation also includes ligating, crosslinking or otherwise bonding a phenylboronated oligopeptide to a cargo molecule. The phenylboronate groups are optionally conjugated to the cargo molecule via linking moieties that can be selectively cleaved. The invention includes certain phenylboronates which are boronation reagents, certain boronated oligopeptides and certain boronated peptides and proteins. The invention also includes kits for enhancing cellular uptake of cargo molecules by boronation with one or more phenylboronates or boronated oligopeptides.

  增强货物分子细胞摄取的方法，通过将货物分子硼酸化，特别是与一个或多个苯硼酸基团硼酸化。细胞摄取至少包括部分摄取到细胞质中。硼酸化包括将一个或多个含有反应基团的取代苯硼酸与货物分子连接、交联或以其他方式键合。硼酸化还包括将苯硼酸化的寡肽与货物分子连接、交联或以其他方式键合。可选地，苯硼酸基团通过可以选择性切割的连接基团与货物分子连接。本发明包括某些作为硼酸化试剂的苯硼酸、某些硼酸化的寡肽以及某些硼酸化的肽和蛋白质。本发明还包括通过用一种或多种苯硼酸或硼酸化寡肽硼酸化来增强货物分子细胞摄取的试剂盒。
• Multifunctional cross-linking reagents. I. Synthesis and properties of novel photoactivable, thiol-directed fluorescent reagents.
  作者：YUICHI KANAOKA、AKIHIKO KOBAYASHI、EISUKE SATO、HITOSHI NAKAYAMA、TAKASHI UENO、DAISAKU MUNO、TAKAMITSU SEKINE

  DOI：10.1248/cpb.32.3926

  日期：——

  Bifunctional photo-activable fluorescent thiol reagents of a new type were synthesized. A maleimide group was bonded to an azidocoumarin group via a methylene chain as a spacer. Reagents of this type react first with a cysteine residue of a protein through the maleimide group, and then form another bond with an amino acid side chain of the protein upon irradiation with light, through a nitrene group formed from the azide. Although the reagent is non-fluorescent, the products are highly fluorescent. The fluorescence characteristics of model compounds of these reagents are also described.

  一种新型双功能光激活荧光硫醇试剂被合成出来。通过一个亚甲基链作为间隔，一个马来酰亚胺基团与一个叠氮香豆素基团相连。这类试剂首先通过马来酰亚胺基团与蛋白质的半胱氨酸残基反应，然后在光照下通过叠氮基团生成的氮烯与蛋白质的氨基酸侧链形成另一个键。虽然试剂本身不发荧光，但其产物具有高度荧光性。还描述了这些试剂模型化合物的荧光特性。
• Evaluation of thioamides, thiolactams and thioureas as hydrogen sulfide (H2S) donors for lowering blood pressure
  作者：Ewelina Zaorska、Tomasz Hutsch、Marta Gawryś-Kopczyńska、Ryszard Ostaszewski、Marcin Ufnal、Dominik Koszelewski

  DOI：10.1016/j.bioorg.2019.102941

  日期：2019.7

  Hydrogen sulfide (H2S) is a biologically important gaseous molecule that exhibits promising protective effects against a variety of pathological processes. For example, it was recognized as a blood pressure lowering agent. Aligned with the need for easily modifiable platforms for the H2S supply, we report here the preparation and the H2S release kinetics from a series of structurally diversified thioamides

  硫化氢（H2S）是生物学上重要的气态分子，对各种病理过程均显示出有希望的保护作用。例如，它被认为是降血压剂。为了满足对H2S供应的易于修改的平台的需求，我们在此报告了一系列结构多样化的硫代酰胺，硫代内酰胺和硫脲的制备和H2S释放动力学。基于五硫化二磷和Lawesson试剂的使用，使用了三种不同的硫磺化方法来制备目标硫代酰胺和硫代内酰胺。此外，在体内和体外研究中都评估了获得的H2S供体。测定了释放出的H2S的动力学参数，并使用两种不同的检测技术将其与NaHS和GYY4137进行了比较：荧光标记7-叠氮基-4-甲基-2H-铬-2--2-和5,5'-二硫代双（2-硝基苯甲酸），巯基探针，也称为Ellman试剂。我们已经证明，通过结构修饰可以控制从这些化合物释放H2S的量。最后，本研究显示了在麻醉大鼠中静脉注射发达供体的降压反应。
• [EN] CARBONIC ANHYDRASE INHIBITORS WITH ANTIMETASTATIC ACTIVITY<br/>[FR] INHIBITEURS D'ANHYDRASE CARBONIQUE PRÉSENTANT UNE ACTIVITÉ ANTIMÉTASTATIQUE
  申请人：METASIGNAL THERAPEUTICS INC

  公开号：WO2012070024A1

  公开（公告）日：2012-05-31

  Compositions for the treatment of cancer comprising coumarin and thiocoumarin derivatives of Formulas I- XII are disclosed. Said derivatives preferentially inhibit carbonic anhydrase IX and XII (which are associated with hypoxic and metastatic tumours) over inhibiting carbonic anhydrase I and II activity. The compositions therefore are suited for treatment of hypoxic or metastatic cancers due to this selective mechanism of action.

  本发明揭示了用于治疗癌症的组合物，包括公开的具有I-XII式的香豆素和硫代香豆素衍生物。所述衍生物优先抑制与低氧和转移性肿瘤相关的碳酸酐酶IX和XII，而不是抑制碳酸酐酶I和II的活性。因此，这些组合物由于这种选择性作用机制而适用于治疗低氧或转移性癌症。