5’-chloro-2’,4-dihydroxychalcone | 93513-92-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 5’-chloro-2’,4-dihydroxychalcone
• 英文别名: 1-(5-Chloro-2-hydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
• CAS: 93513-92-9
• 化学式: C₁₅H₁₁ClO₃
• 分子量: 274.704
• InChiKey: KXLQQFWERKUYLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5’-chloro-2’,4-dihydroxychalcone 在 溴 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以63%的产率得到
  参考文献：
  名称：

  Basawaraj, Raga; Alvi, Shah Nadeemuddin; Chillargi, Neelavati, Indian Journal of Heterocyclic Chemistry, 2011, vol. 21, # 2, p. 147 - 150

  摘要：

  DOI：
• 作为产物：
  描述：

  5'-chloro-2'-hydroxy-4-(methoxymethoxy)chalcone 在 硫酸 、 溶剂黄146 作用下， 以52%的产率得到5’-chloro-2’,4-dihydroxychalcone
  参考文献：
  名称：

  5′-Chloro-2,2′-dihydroxychalcone and related flavanoids as treatments for prostate cancer

  摘要：

  Several flavonoids and their biosynthetic precursor chalcones were designed and synthesized to improve the biological effects of the lead compound 2'-hydroxyflavonone against androgen receptor (AR)-dependent transcriptional stimulation. Newly synthesized chalcones 19 and 26 suppressed AR dependent transcription as well as DHT-dependent growth stimulation at a low micromolar level. These compounds were also effective against ligand-independent constitutively active mutant AR derived from castration-resistant PCa (CRPC). Compounds 19 and 26 showed broad spectrum anti-proliferative activity at 5-10 mu M against multiple tumor cell lines including androgen-independent and taxane-resistant prostate cancer as well as a multidrug-resistant subline. Mode of action studies suggested that 19 induced sub-G1 accumulation in PC-3 cells by disrupting the microtubule network without affecting cell cycle progression. Furthermore, the in vivo effectiveness of chalcone 19 was confirmed in a xenograft model antitumor assay. Thus, chalcone 19 has the potential to be a bifunctional lead for treatment of AR-dependent PCa at lower doses as well as AR-independent PCa, including CRPC, at higher doses. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.08.069

文献信息

• Phototransformations of some 3‐cyclohexenyloxychromenones: Synthesis of Spirocyclic compounds
  作者：Radhika Khanna、Aarti Dalal、Urmila Berar、Sandeep Singh、Ramesh C. Kamboj

  DOI：10.1002/jccs.201800329

  日期：2019.6

  The phototransformation of the 3‐cyclohexenyloxychromenones by irradiation with a pyrex‐filtered light from a 125 W Hg vapor lamp under an inert atmosphere into the spirocyclic fused xanthenones was described. The efficacy of the protocol depended upon the position (o‐, m‐, or p‐) of the cyclohexenyloxy group appended to the 2‐aryl moiety on the chromenone nucleus, which was further invoked by steric

  描述了通过在惰性气氛下用125 W Hg蒸气灯的耐热玻璃过滤光辐照3-环己烯基氧色酮到螺环稠合的蒽酮的光转化。该协议的有效性取决于环己烯氧基在色酮核上2-芳基部分附加的位置（o-，m-或p-），这在空间，电子和邻近方面都需要进一步考虑。使用光谱数据（IR和NMR）确定基材和光产物的结构。
• Synthesis and Anticancer Activity of Novel Thiazolo-Coumarin Derivatives
  作者：R. Swethan Babu、Senthilkumar Palaniappan、M.K. Kathiravan

  DOI：10.14233/ajchem.2023.27263

  日期：2023.1.15

  As a starting point for creating new inhibitor scaffolds, a molecular hybridization approach was applied in designing the novel molecules using coumarin-thiazole hybrids as mPGES-1 enzyme inhibitors. Thus, in present work, the novel thiazolo coumarin derivatives (8-35) were synthesized and characterized by 1H NMR, IR and ESI-MS spectra. All the synthesized molecules (8-35) were also investigated for their anticancer activity on MCF-7 (breast cancer), caco-2 (colon cancer), HeLa (Cervix cancer) cell lines. Studies revealed that compounds (8-14) and (22-28) showed inhibition (IC50) at different concentrations of 12.5, 50, 100 μg/mL and more than 100 μg/mL.

  作为创建新抑制剂支架的起点，我们采用分子杂交方法 分子杂交法设计新型分子，将香豆素-噻唑杂化物用作 mPGES-1 酶抑制剂。 因此，在本研究中，合成了新型噻唑香豆素衍生物 (8-35)，并通过 1H NMR、IR 1H NMR、IR 和 ESI-MS 光谱。还研究了所有合成分子（8-35）对 MCF 细胞的抗癌活性。 对 MCF-7（乳腺癌）、caco-2（结肠癌）和 HeLa（宫颈癌）细胞系的抗癌活性进行了研究。 细胞系的抗癌活性。研究结果表明，化合物（8-14）和（22-28）在不同浓度（12.5 浓度分别为 12.5、50、100 μg/mL 和超过 100 μg/mL。
• Kamboj, Ramesh C.; Berar, Urmila; Berar, Surinder, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 5, p. 685 - 691
  作者：Kamboj, Ramesh C.、Berar, Urmila、Berar, Surinder、Thakur, Mandeep、Gupta, Satish C.

  DOI：——

  日期：——
• 5′-Chloro-2,2′-dihydroxychalcone and related flavanoids as treatments for prostate cancer
  作者：Yohei Saito、Atsushi Mizokami、Hiroyuki Tsurimoto、Kouji Izumi、Masuo Goto、Kyoko Nakagawa-Goto

  DOI：10.1016/j.ejmech.2018.08.069

  日期：2018.9

  Several flavonoids and their biosynthetic precursor chalcones were designed and synthesized to improve the biological effects of the lead compound 2'-hydroxyflavonone against androgen receptor (AR)-dependent transcriptional stimulation. Newly synthesized chalcones 19 and 26 suppressed AR dependent transcription as well as DHT-dependent growth stimulation at a low micromolar level. These compounds were also effective against ligand-independent constitutively active mutant AR derived from castration-resistant PCa (CRPC). Compounds 19 and 26 showed broad spectrum anti-proliferative activity at 5-10 mu M against multiple tumor cell lines including androgen-independent and taxane-resistant prostate cancer as well as a multidrug-resistant subline. Mode of action studies suggested that 19 induced sub-G1 accumulation in PC-3 cells by disrupting the microtubule network without affecting cell cycle progression. Furthermore, the in vivo effectiveness of chalcone 19 was confirmed in a xenograft model antitumor assay. Thus, chalcone 19 has the potential to be a bifunctional lead for treatment of AR-dependent PCa at lower doses as well as AR-independent PCa, including CRPC, at higher doses. (C) 2018 Elsevier Masson SAS. All rights reserved.
• Basawaraj, Raga; Alvi, Shah Nadeemuddin; Chillargi, Neelavati, Indian Journal of Heterocyclic Chemistry, 2011, vol. 21, # 2, p. 147 - 150
  作者：Basawaraj, Raga、Alvi, Shah Nadeemuddin、Chillargi, Neelavati、Gahininath, Wadikar、Zaheeruddin

  DOI：——

  日期：——