4-bromomethyl-7-carboethoxyaminocoumarin | 120402-74-6

• 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: 4-bromomethyl-7-carboethoxyaminocoumarin
• 英文别名: ethyl N-[4-(bromomethyl)-2-oxochromen-7-yl]carbamate
• CAS: 120402-74-6
• 化学式: C₁₃H₁₂BrNO₄
• 分子量: 326.147
• InChiKey: PYVUVBWTAFMGOR-UHFFFAOYSA-N

物化性质

• 熔点：
  219-221 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  400.1±45.0 °C(Predicted)
• 密度：
  1.588±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  4-bromomethyl-7-carboethoxyaminocoumarin 在 硫酸 、 溶剂黄146 、 sodium sulfite 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 10.0h， 生成 triethylammonium 7-(N-tosyl-L-phenylalanyl)coumarinylamido-4-methanesulfonate
  参考文献：
  名称：

  New water-soluble fluorogenic amine. 7-Aminocoumarin-4-methanesulfonic acid(ACMS) and related substrates for proteinases.

  摘要：

  描述了一种水溶性荧光氨基化合物——7-氨基香豆酸-4-美克苏磺酸（ACMS，5）的合成及其性质。合成了几种5的肽酰胺，并作为新的荧光底物进行了检验，适用于凝乳酶、胰蛋白酶及相关酶。

  DOI：

  10.1248/cpb.36.3496
• 作为产物：
  描述：

  4-溴乙酰乙酸乙酯 、 (3-羟基-苯基)-氨基甲酸乙酯 在 硫酸 作用下， 以38%的产率得到4-bromomethyl-7-carboethoxyaminocoumarin
  参考文献：
  名称：

  New water-soluble fluorogenic amine. 7-Aminocoumarin-4-methanesulfonic acid(ACMS) and related substrates for proteinases.

  摘要：

  描述了一种水溶性荧光氨基化合物——7-氨基香豆酸-4-美克苏磺酸（ACMS，5）的合成及其性质。合成了几种5的肽酰胺，并作为新的荧光底物进行了检验，适用于凝乳酶、胰蛋白酶及相关酶。

  DOI：

  10.1248/cpb.36.3496

文献信息

• Synthesis of Coumarin-benzotriazole Hybrids and Evaluation of their Anti-tubercular Activity
  作者：Sachin P. Ambekar、Chakrabhavi Dhananjaya Mohan、Arunkumar Shirahatti、Mahesh K. Kumar、Shobith Rangappa、Surender Mohan、Basappa、Obelannavar Kotresh、Kanchugarakoppal S. Rangappa

  DOI：10.2174/1570178614666170710125501

  日期：2017.12.11

  Background: Tuberculosis is one of the top ranked airborne infectious diseases caused by the bacillus Mycobacterium tuberculosis with high mortality rate from a single infectious agent. In the present article, we aimed to synthesize oxadiazole-coumarin-triazole based small molecules and evaluate for their possible anti-mycobacterial activity. Method: Herein, we describe the facile synthesis of 5-((1H-benzo[d][1,2,3]triazol-1-yl)methyl)-1,3,4- oxadiazole-2-thiol-tethered substituted 4-(bromomethyl)-7-methyl-2H-chromen-2-one derivatives and evaluated for their anti-mycobacterial activity against H37Rv strain of M. tuberculosis. We also evaluated the cytotoxic effect of new compounds on normal cells. Results: Among the 14 novel oxadiazole-coumarin-triazole derivatives, 4-((5-((1H-benzo[d][1,2,3]triazol-1- yl)methyl)-1,3,4-oxadiazol-2-ylthio)methyl)-6-methoxy-2H-chromen-2-one (5f) displayed good antimycobacterial activity towards M. tuberculosis with an MIC value of 15.5 µM. Pyrazinamide was used as reference drug. Our investigation also revealed that, 5f is not cytotoxic to normal cells. Conclusion: In summary, the findings suggested that novel 1,3,4-oxadiazole coumarin-triazole hybrids are promising antimycobacterial agents against M. tuberculosis.

  背景：结核病是由结核分枝杆菌引起的高度致死性空气传播传染病之一。在本文中，我们的目标是合成基于噁二唑-香豆素-三唑的小分子并评估它们可能的抗结核活性。 方法：在此，我们描述了5-((1H-苯并[d][1,2,3]三唑-1-基)甲基)-1,3,4-噁二唑-2-硫醇缀合的取代4-(溴甲基)-7-甲基-2H-色烯-2-酮衍生物的简易合成，并评估了它们对M. tuberculosis H37Rv菌株的抗结核活性。我们还评估了新化合物对正常细胞的细胞毒性效应。 结果：在14种新型噁二唑-香豆素-三唑衍生物中，4-((5-((1H-苯并[d][1,2,3]三唑-1-基)甲基)-1,3,4-噁二唑-2-基硫)甲基)-6-甲氧基-2H-色烯-2-酮(5f)显示出对M. tuberculosis的良好抗菌活性，MIC值为15.5 µM。利福平被用作参考药物。我们的研究还揭示，5f对正常细胞没有细胞毒性。 结论：总之，研究结果表明，新型1,3,4-噁二唑香豆素-三唑杂化物是针对M. tuberculosis有前景的抗结核药物。
• A dual-analyte probe: hypoxia activated nitric oxide detection with phototriggered drug release ability
  作者：Sandipan Biswas、Y. Rajesh、Shrabani Barman、Manoranjan Bera、Amrita Paul、Mahitosh Mandal、N. D. Pradeep Singh

  DOI：10.1039/c8cc01854e

  日期：——

  A new strategy for the detection of hypoxia and NO succeeded by photocontrolled delivery of an anticancer agent has been demonstrated. The developed system is able to produce distinct responses (dual channel) upon interaction with hypoxia and NO. This probe can also release anticancer drugs upon photoirradiation acting potentially as both a dual-analyte imaging agent and a prodrug.

  已经证明了通过光控递送抗癌药成功检测缺氧和NO的新策略。与缺氧和NO相互作用时，开发的系统能够产生不同的响应（双通道）。该探针还可以在光辐照后释放抗癌药，可能同时充当双重分析物显像剂和前药。
• Novel synthetic coumarins that targets NF-κB in Hepatocellular carcinoma
  作者：Mahabaleshwaraiah Neelgundmath、Koragere Rajashekar Dinesh、Chakrabhavi Dhananjaya Mohan、Feng Li、Xiaoyun Dai、Kodappully Sivaraman Siveen、Shardul Paricharak、Daniel J. Mason、Julian E. Fuchs、Gautam Sethi、Andreas Bender、Kanchugarakoppal S. Rangappa、Obelannavar Kotresh、Basappa

  DOI：10.1016/j.bmcl.2014.12.065

  日期：2015.2

  Hepatocellular carcinoma (HCC) is the fifth most common malignant tumor worldwide, and is the third most common cause of cancer related death. Constitutive activation of NF-kappa B is the underlying mechanism behind tumorigenesis and this protein regulates the expression of genes involved in proliferation, survival, drug resistance, angiogenesis and metastasis. The design of inhibitors which suppress NF-kappa B activation is therefore of great therapeutic importance in the treatment of HCC. In this study, we investigated the effect of newly synthesized coumarin derivatives against HCC cells, and identified (7-Carbethoxyamino-2-oxo-2H-chromen-4-yl)methylpyrrolidine-1 carbodithioate (CPP) as lead compound. Further, we evaluated the effect of CPP on the DNA binding ability of NF-kappa B, CXCL12-induced cell migration and invasion, and the regulated gene products in HCC cells. We found that CPP induced cytotoxicity in three HCC cells in a time and dose dependent manner, and suppressed the DNA binding ability of NF-kappa B. CPP significantly decreased the CXCL12-induced cell migration and invasion. More evidently, CPP inhibits the expression of NF-kappa B targeted genes such as cyclin D1, Bcl-2, survivin, MMP12 and C-Myc. Furthermore, the molecular docking analysis suggested that CPP interacts with the p50 binding domain of the p65 sub-unit, scoring best among the 26 docked coumarin derivatives of this study. Thus, we are reporting CPP as a potent inhibitor of the pro-inflammatory pathway in Hepatocellular carcinoma. (C) 2014 Elsevier Ltd. All rights reserved.
• SATO, EISUKE;MATSUHISA, AKIRA;SAKASHITA, MARI;KANAOKA, YUICHI, CHEM. AND PHARM. BULL., 36,(1988) N 9, C. 3496-3502
  作者：SATO, EISUKE、MATSUHISA, AKIRA、SAKASHITA, MARI、KANAOKA, YUICHI

  DOI：——

  日期：——