tert-butyl 4-methyl-2-oxo-2H-chromen-7-ylcarbamate | 1174286-59-9

• 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: tert-butyl 4-methyl-2-oxo-2H-chromen-7-ylcarbamate
• 英文别名: 7-(tert-butoxycarbonylamino)-4-methyl coumarin；tert-butyl N-(4-methyl-2-oxochromen-7-yl)carbamate
• CAS: 1174286-59-9
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: PMMDIGKKLWVZFC-UHFFFAOYSA-N

物化性质

• 沸点：
  373.8±37.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-methyl-2-oxo-2H-chromen-7-ylcarbamate 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 sodium carbonate 、 三苯基膦 、 三氟乙酸 、 苯酚 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 111.0h， 生成
  参考文献：
  名称：

  一对[2]轮烷的五态分子穿梭：响应酸和碱刺激的不同输出。

  摘要：

  在这项研究中，我们合成了两种酸/碱可控制的[2]轮烷，分别以氨基重氮苯和氨基香豆素单元为生色团，分别以二苯并[24] crown-8和二苯并[25] crown-8单元为大环组分。 。每个[2]轮烷含有N-烷基芳基胺（铵）和N，N-二烷基胺（铵）以其冠醚成分的结合位点为中心。发色团的吸收方式取决于所包围的大环组分的位置和质子化的程度，每种[2]轮烷都有明显的三种不同状态（在酸性，中性和碱性条件下）。混合的[2]轮烷化合物体系根据添加的酸或碱的量和强度，根据氨基的质子化程度显示出逐步和独立的分子穿梭行为。这样，该系统提供了五个不同的吸收信号作为输出，可以使用UV / Vis光谱法读取该信号。

  DOI：

  10.1002/asia.201600743
• 作为产物：
  描述：

  羟甲香豆素 在 potassium phosphate 、 [(2-di-tert-butylphosphino-2′,4′,6′-triisopropyl-1, 1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)] palladium(II) methanesulfonate 、 potassium carbonate 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 18.0h， 生成 tert-butyl 4-methyl-2-oxo-2H-chromen-7-ylcarbamate
  参考文献：
  名称：

  酰胺和酰胺衍生物与壬二酸伞形酮的交叉偶联：香豆素衍生物和荧光材料的合成。

  摘要：

  描述了4-甲基伞形酮衍生的壬二酸酯与酰胺，氨基甲酸酯和磺酰胺之间的布赫瓦尔德-哈特维格交叉偶联反应。以良好至优异的产率制备了多种N-取代的7-氨基香豆素类似物。测定了水溶性衍生物的光物理性质，并且它们显示出基于色素的变化。克级合成提供了一种丙烯酰胺类似物，该丙烯酰胺类似物用于制造可抵抗超纯H 2 O浸出的荧光聚（甲基丙烯酸2-羟乙酯）（pHEMA）水凝胶。我们设想，我们报告的访问7-氨基-该领域的研究人员将发现4-甲基香豆素衍生物可用于开发基于荧光香豆素的新型荧光探针。

  DOI：

  10.1021/acs.joc.0c00813

文献信息

• [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。
• CARBONIC ANHYDRASE INHIBITORS WITH ANTIMETASTATIC ACTIVITY
  申请人：Supuran Claudiu

  公开号：US20140148400A1

  公开（公告）日：2014-05-29

  Derivatized coumarin-based pharmaceutical compositions and methods to use them are provided. The compositions are characterized in that they inhibit the activity of tumor-related CAIX and CAXII to a greater degree than they inhibit the activity of CAI and CAII. The compositions can be used to suppress tumor growth and/or suppress tumor metastases in a mammal.

  提供了衍生香豆素类制药组合物及其使用方法。这些组合物的特征在于它们抑制肿瘤相关的CAIX和CAXII的活性，而不是CAI和CAII的活性。这些组合物可用于抑制哺乳动物中的肿瘤生长和/或抑制肿瘤转移。
• Direct Amidation of <i>N</i>-Boc- and <i>N</i>-Cbz-Protected Amines via Rhodium-Catalyzed Coupling of Arylboroxines and Carbamates
  作者：Diane S. W. Lim、Tedrick T. S. Lew、Yugen Zhang

  DOI：10.1021/acs.orglett.5b03061

  日期：2015.12.18

  N-Boc- and N-Cbz-protected amines are directly converted into amides by a novel rhodium-catalyzed coupling of arylboroxines and carbamates, replacing the traditional two-step deprotection-condensation sequence. Both protected anilines and aliphatic amines are efficiently transformed into a wide variety of secondary benzamides, including sterically hindered and electron-deficient amides, as well as in the presence of acid-labile and reducible functional groups.
• Catalytic Coupling of Arene C–H Bonds and Alkynes for the Synthesis of Coumarins: Substrate Scope and Application to the Development of Neuroimaging Agents
  作者：Paul A. Vadola、Dalibor Sames

  DOI：10.1021/jo3006842

  日期：2012.9.21

  C-H bond functionalization offers strategically novel approaches to complex organic compounds. However, many C-H functionalization reactions suffer from poor compatibility with Lewis basic functional groups, especially amines, which are often essential for biological activity. This study describes a systematic examination of the substrate scope of catalytic hydroarylation in the context of complex amino coumarin synthesis. The choice of substrates was guided by the design and development of the next generation of fluorescent false neurotransmitters (FFNs), neuroimaging probes we recently introduced for optical imaging of neurotransmission in the brain. Comparison of two mild protocols using catalytic PtCl4 or Au(PPh3)Cl/AgSbF6 revealed that each method has a broad and mutually complementary substrate scope. The relatively less active platinum system out-performed the gold catalyst with indole substrates lacking substitution at the C-3 position and provided higher regioselectivity in the case of carbazole-based substrates. On the other hand, the more active gold catalyst demonstrated excellent functional group tolerance, and the ability to catalyze the formation of strained, helical products. The development of these two protocols offers enhanced substrate scope and provides versatile synthetic tools required for the structure-activity examination of FFN neuroimaging probes as well as for the synthesis of complex coumarins in general.
• Novel coumarins and 2-thioxo-coumarins as inhibitors of the tumor-associated carbonic anhydrases IX and XII
  作者：Fabrizio Carta、Alfonso Maresca、Andrea Scozzafava、Claudiu T. Supuran

  DOI：10.1016/j.bmc.2012.02.014

  日期：2012.4

  A series of coumarins incorporating tert-butyl-dimethylsilyloxy- or allyoxy- moieties in positions 4-, 6 or 7 of the heterocyclic ring have been synthesized and then converted to the corresponding 2-thioxocoumarins. Other derivatives incorporating hydroxyethyloxy-, tosylethoxy- and 2-fluroethyloxy-moieties in position 7 of the coumarin ring were synthesized together with derivatives of 4-methyl-7-amino coumarin incorporating acetamido, 3,5-dimethylphenylureido- and tert-butyloxycarbonylamido functionalities. All these compounds were assayed as inhibitors of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1). The human (h) cytosolic isoforms hCA I and II were weakly inhibited (hCA I) or not inhibited at all (hCA II) by these (thioxo) coumarins whereas the tumor-associated transmembrane isoforms hCA IX and XII were inhibited with efficiencies from the submicromolar to the low micromolar range by many of these derivatives. The structure-activity relationship for these classes of less investigated CA inhibitors are delineated, with the potential of using them as leads to obtain isoform-selective inhibitors with excellent affinity for CA IX and XII (validated antitumor targets) which do not significantly inhibit the cytosolic offtarget isoforms hCA I and II. (C) 2012 Elsevier Ltd. All rights reserved.