3-(3-(4-chlorophenyl)prop-2-enoyl)-4-hydroxy-2H-1-benzopyran-2-one | 57339-66-9

• 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: 3-(3-(4-chlorophenyl)prop-2-enoyl)-4-hydroxy-2H-1-benzopyran-2-one
• 英文别名: (E)-4-Hydroxy 3-(3-(4-chlorophenyl)acryloyl)-2H-chromen-2-one；3-[3-(4-Chlorophenyl)prop-2-enoyl]-4-hydroxychromen-2-one
• CAS: 57339-66-9
• 化学式: C₁₈H₁₁ClO₄
• 分子量: 326.736
• InChiKey: DSRXGQBADCHUPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• 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：

  3-(3-(4-chlorophenyl)prop-2-enoyl)-4-hydroxy-2H-1-benzopyran-2-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  作为抗黑色素瘤药物的新型吡唑基二氢吲哚啉-2-一香豆素衍生物：设计、合成、BRAFV600E/VEGFR-2 双重抑制和计算研究

  摘要：

  恶性黑色素瘤是最具侵袭性的皮肤癌，死亡风险最高。 BRAF V600E的抑制似乎与克服黑色素瘤治疗期间产生的继发耐药性相关。 BRAF V600E通过修饰血管生成诱导剂的表达来触发血管生成，这在黑色素瘤的转移中发挥着至关重要的作用。因此，BRAF V600E /VEGFR-2信号通路的双重抑制被认为是设计抗黑色素瘤候选药物的合理方法。在这项研究中，设计了一类新的吡唑基林多林-2-单连接香豆素衍生物作为靶向 A375 黑色素瘤细胞的 BRAF V600E /VEGFR-2 双重抑制剂。目标化合物经过定制以占据 BRAF V600E和 VEGFR-2 的口袋。大多数合成的化合物对 A375 细胞表现出有效的平均生长抑制活性。化合物4j是最活跃的细胞毒性衍生物，在0.96 μM的低微摩尔浓度下显示出IC 50值，并具有显着的安全性。此外， 4j对 BRAF V600E和 VEGFR-2 显示出双重有效抑制活性（IC

  DOI：

  10.1039/d4ra00157e
• 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 3-(3-(4-chlorophenyl)prop-2-enoyl)-4-hydroxy-2H-1-benzopyran-2-one
  参考文献：
  名称：

  作为抗黑色素瘤药物的新型吡唑基二氢吲哚啉-2-一香豆素衍生物：设计、合成、BRAFV600E/VEGFR-2 双重抑制和计算研究

  摘要：

  恶性黑色素瘤是最具侵袭性的皮肤癌，死亡风险最高。 BRAF V600E的抑制似乎与克服黑色素瘤治疗期间产生的继发耐药性相关。 BRAF V600E通过修饰血管生成诱导剂的表达来触发血管生成，这在黑色素瘤的转移中发挥着至关重要的作用。因此，BRAF V600E /VEGFR-2信号通路的双重抑制被认为是设计抗黑色素瘤候选药物的合理方法。在这项研究中，设计了一类新的吡唑基林多林-2-单连接香豆素衍生物作为靶向 A375 黑色素瘤细胞的 BRAF V600E /VEGFR-2 双重抑制剂。目标化合物经过定制以占据 BRAF V600E和 VEGFR-2 的口袋。大多数合成的化合物对 A375 细胞表现出有效的平均生长抑制活性。化合物4j是最活跃的细胞毒性衍生物，在0.96 μM的低微摩尔浓度下显示出IC 50值，并具有显着的安全性。此外， 4j对 BRAF V600E和 VEGFR-2 显示出双重有效抑制活性（IC

  DOI：

  10.1039/d4ra00157e

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.
• Abdel Hafez, Omiama M.; Nassar, Mahmoud I.; El-Kousy, Salah M., Acta poloniae pharmaceutica, 2014, vol. 71, # 4, p. 593 - 601
  作者：Abdel Hafez, Omiama M.、Nassar, Mahmoud I.、El-Kousy, Salah M.、Abdel-Razik, Ayman F.、Atalla, Sherien M. M.、El-Ghonemy, Mai M.

  DOI：——

  日期：——