| 57339-68-1

• 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
• CAS: 57339-68-1
• 化学式: C₁₈H₁₁ClO₄
• 分子量: 326.736
• InChiKey: XRIMWNNBWYYOPF-UHFFFAOYSA-N

物化性质

• 沸点：
  536.9±50.0 °C(Predicted)
• 密度：
  1.470±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.51
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  以 乙醇 为溶剂， 反应 1.0h， 以88%的产率得到3-(5-(2-chlorophenyl)-4,5-dihydro-1H-pyrazol-3-yl)-4-hydroxy-2H-chromen-2-one
  参考文献：
  名称：

  3-取代的-4-羟基香豆素作为一种新型支架，具有有效的CDK抑制作用和有希望的抗癌作用：合成，分子建模和QSAR研究。

  摘要：

  设计，合成并评估了一系列新的3-取代-4-羟基香豆素衍生物的CDK抑制和抗癌活性。与flavopiridol相比，所有合成的目标化合物均对CDK1B表现出极高的亲和力和选择性，Ki值在低纳摩尔范围内（Ki = 0.35-0.88nM）。它们中的大多数引起对CDK9T1的显着抑制作用（Ki ＝ 3.26-23.45nM）。此外，所有目标化合物均针对18种类型的人类肿瘤细胞系进行了体外测试。hydr 3a，N-苯基吡唑啉衍生物6b和2-氨基吡啶基-3-甲腈衍生物8c是针对MCF-7乳腺癌细胞系的最有效抗癌剂（分别为IC50 = 0.21、0.21和0.23nM）。目标化合物3a，在MCF-7乳腺癌小鼠异种移植模型中进一步评估了6b和8c，并显示了10mg / kg剂量的体内功效。对接研究证实了CDK1B活性位点的独特结合模式，其得分高于黄酮哌啶醇。定量结构活动关系研究已经完成，揭示了0.81的高度预测力R（2）。

  DOI：

  10.1016/j.bioorg.2016.06.005
• 作为产物：
  描述：

  4-羟基香豆素 在 哌啶 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  3-取代的-4-羟基香豆素作为一种新型支架，具有有效的CDK抑制作用和有希望的抗癌作用：合成，分子建模和QSAR研究。

  摘要：

  设计，合成并评估了一系列新的3-取代-4-羟基香豆素衍生物的CDK抑制和抗癌活性。与flavopiridol相比，所有合成的目标化合物均对CDK1B表现出极高的亲和力和选择性，Ki值在低纳摩尔范围内（Ki = 0.35-0.88nM）。它们中的大多数引起对CDK9T1的显着抑制作用（Ki ＝ 3.26-23.45nM）。此外，所有目标化合物均针对18种类型的人类肿瘤细胞系进行了体外测试。hydr 3a，N-苯基吡唑啉衍生物6b和2-氨基吡啶基-3-甲腈衍生物8c是针对MCF-7乳腺癌细胞系的最有效抗癌剂（分别为IC50 = 0.21、0.21和0.23nM）。目标化合物3a，在MCF-7乳腺癌小鼠异种移植模型中进一步评估了6b和8c，并显示了10mg / kg剂量的体内功效。对接研究证实了CDK1B活性位点的独特结合模式，其得分高于黄酮哌啶醇。定量结构活动关系研究已经完成，揭示了0.81的高度预测力R（2）。

  DOI：

  10.1016/j.bioorg.2016.06.005

文献信息

• Synthesis of Some Coumarinyl Chalcones and their Antiproliferative Activity Against Breast Cancer Cell Lines
  作者：Kuldeep Patel、Chandrabose Karthikeyan、Viswas Raja Solomon、N. S. Hari Narayana Moorthy、Hoyun Lee、Kapendra Sahu、Girdhar Singh Deora、Piyush Trivedi

  DOI：10.2174/157018011794839475

  日期：2011.5.1

  A series of coumarinyl chalcones derivatives were synthesized and evaluated for their antiproliferative activities on three different breast cancer cell lines (MDA-MB231, MDA-MB468, MCF7) and one non-cancer breast epithelial cell line (184B5). The coumarinyl derivatives exhibited anticancer activity against breast cancer cell lines at a micromolar range. A structure-activity relationship (SAR) analysis was performed by studying the effect of substituents on their antiproliferative activities. One of the compound 3i bearing methoxy substitutions at the R1, R2 and R3 positions of the phenyl ring showed comparable potency to the reference drug cisplatin as well as a two-fold higher selectivity for the breast cancer cell lines than 184B5 cells.

  研究人员合成了一系列香豆素基查尔酮衍生物，并评估了它们对三种不同乳腺癌细胞系（MDA-MB231、MDA-MB468、MCF7）和一种非癌症乳腺上皮细胞系（184B5）的抗增殖活性。香豆素基衍生物对乳腺癌细胞株具有微摩尔范围的抗癌活性。通过研究取代基对其抗增殖活性的影响，进行了结构-活性关系（SAR）分析。其中一个在苯环的 R1、R2 和 R3 位置上带有甲氧基取代基的化合物 3i 显示出与参考药物顺铂相当的效力，而且对乳腺癌细胞株的选择性比 184B5 细胞高出两倍。
• Antileishmanial activity of novel indolyl–coumarin hybrids: Design, synthesis, biological evaluation, molecular docking study and in silico ADME prediction
  作者：Jaiprakash N. Sangshetti、Firoz A. Kalam Khan、Abhishek A. Kulkarni、Rajendra H. Patil、Amol M. Pachpinde、Kishan S. Lohar、Devanand B. Shinde

  DOI：10.1016/j.bmcl.2015.12.085

  日期：2016.2

  performing molecular docking studies, it was found that compounds 13a and 13d had potential to inhibit pteridine reductase 1 enzyme. In silico ADME pharmacokinetic parameters had shown promising results and none of the synthesized compounds had violated Lipinski’s rule of five. Thus, suggesting that compounds from the present series can serve as important gateway for the design and development of new antileishmanial

  在目前的工作中，我们已经设计和合成了总共十二种新颖的3-（3-（1 H-吲哚-3-基）-3-苯基丙酰基）-4-羟基-2 H-铬-2--2-酮衍生物13（a – l），使用掺有Ho 3+的CoFe 2 O 4纳米颗粒作为催化剂，并评估了其潜在的抗菌活性和抗氧化活性。与标准的葡糖基葡萄糖酸钠（IC 50）相比，发现化合物13a，13d和13h具有显着的抗霉菌活性（IC 50值分别为95.50、95.00和99.00μg/ mL）。 = 490.00μg/ mL）。化合物13a（IC 50  = 12.40μg/ mL），13d（IC 50  = 13.49μg/ mL），13g（IC 50  = 13.24μg/ mL）和13l（IC 50  = 13.74μg/ mL）具有良好的抗氧化活性与标准丁基化羟基甲苯（IC 50  = 16.5μg/ mL）和抗坏血酸（IC 50  = 12.8μg/
• Evaluation of Structurally Diverse Benzoazepines Clubbed with Coumarins as<i>Mycobacterium tuberculosis</i>Agents
  作者：Kuldip Upadhyay、Atul Manvar、Kena Rawal、Sudhir Joshi、Jalpa Trivedi、Ravi Chaniyara、Anamik Shah

  DOI：10.1111/j.1747-0285.2012.01436.x

  日期：2012.12

  Tuberculosis caused by Mycobacterium tuberculosis remains a leading cause of mortality worldwide into 21st century. In continuation with our anti‐tuberculosis research programme, in this work, we have prepared molecularly diverse coumarins clubbed with benzothiazepines as well as its aza‐analogues‐benzodiazepines by molecular hybridization. The resulting compounds were screened for their M. tuberculosis activity against H37Rv strains using microplate alamar blue assay. Among the designed diversity, the compounds 5k, 5n and 5o were found significantly active in primary anti‐tuberculosis assay at minimum inhibitory concentration <6.25 μm. Moreover, the IC50 values of 5k and 5o in level‐2 screening were observed as >10 μg/mL and 3.63 μg/mL, respectively. Design and synthesis of more focused library and its three‐dimensional quantitative structure activity relationship analysis are underway.
• Design, synthesis and biological evaluation of some novel 3-cinnamoyl-4-hydroxy-2H-chromen-2-ones as antimalarial agents
  作者：Kuldeep Patel、Chandrabose Karthikeyan、N. S. Hari Narayana Moorthy、Girdhar Singh Deora、Viswas Raja Solomon、Hoyun Lee、Piyush Trivedi

  DOI：10.1007/s00044-011-9694-1

  日期：2012.8

  A novel series of 3-cinnamoyl-4-hydroxy-2H-chromen-2-ones were designed, synthesized and screened for antiplasmodial activity. Eleven compounds of the series exhibited micromolar potency against chloroquine sensitive and chloroquine resistant strains. The most potent compound 4-hydroxy-3-(3-(4-nitrophenyl)acryloyl)-2H-chromen-2-one showed inhibitory potency (IC50) of 3.1 and 4 mu g/ml against chloroquine sensitive and chloroquine resistant strains, respectively. A structure activity relationship study was performed by correlating the effect of substituents with the antimalarial activity of the title compounds. The novel 3-cinnamoyl-4-hydroxy-2H-chromen-2-ones reported here should be good lead for further development of antimalarial agents that can overcome resistance.