BG0101 | 31184-84-6

• 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: BG0101
• 英文别名: (E)-3-(4-chlorophenyl)-1-(2,4-dimethoxyphenyl)prop-2-en-1-one；1-(2,4-dimethoxyphenyl)-3-(4-chlorophenyl)prop-2-enone；(2E)-3-(4-chlorophenyl)-1-(2,4-dimethoxyphenyl)prop-2-en-1-one
• CAS: 31184-84-6
• 化学式: C₁₇H₁₅ClO₃
• 分子量: 302.757
• InChiKey: SIPIMPITDGVGQS-BJMVGYQFSA-N

物化性质

• 沸点：
  473.4±45.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  BG0101 在 乙酸铵 作用下， 以 吡啶 为溶剂， 反应 10.0h， 生成 5-(4-Chloro-phenyl)-7-(2,4-dimethoxy-phenyl)-4-imino-1,4-dihydro-pyrido[2,3-d][1,3]thiazine-2-thione
  参考文献：
  名称：

  Salem, Mounir A. I.; Madkour, Hassan M. F.; Soliman, El-Sayed A., Heterocycles, 2000, vol. 53, # 5, p. 1129 - 1143

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氯苯甲醛 、 2,4-二甲氧基苯乙酮 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以36.4%的产率得到BG0101
  参考文献：
  名称：

  抗疟疾烷氧基化和羟基化的查耳酮[校正]：结构-活性关系分析。

  摘要：

  合成在环B上具有2'，3'，4'-三甲氧基，2'，4'-二甲氧基，4'-甲氧基，4'-乙氧基，2'，4'-二羟基和4'-羟基的邻苯二甲酰并在[3H]次黄嘌呤摄取测定中针对恶性疟原虫（K1）进行了体外评估。另一个环A是具有不同亲脂性的给电子或吸电子取代基的喹啉，吡啶，萘或苯环。三甲氧基6和27，二甲氧基7，8，29和甲氧基31类似物具有良好的体外活性（IC（50）<5 microM）。在活性化合物中很好地代表了3-喹啉基环A衍生物。羟基查耳酮的活性低于相应的烷氧基化类似物。在体内评估时，8和208在延长被感染小鼠的寿命方面与氯喹相当。多变量数据分析表明，体外活性主要取决于环B的特性。使用对潜在结构的投影，获得了各种B环查耳酮具有令人满意的预测能力的定量构效关系模型。提出了一个具有良好可预测性的模型，用于19个活动查尔肯。尺寸和疏水性被确定为关键参数。

  DOI：

  10.1021/jm0101747

文献信息

• Design and synthesis of novel 1,3,5-triphenyl pyrazolines as potential anti-inflammatory agents through allosteric inhibition of protein kinase Czeta (PKCζ)
  作者：Mohammad Abdel-Halim、Ashraf H. Abadi、Matthias Engel

  DOI：10.1039/c8md00100f

  日期：——

  Much light has been shed on the vital role of protein kinase Czeta (PKCζ) in NF-κB activation and the potential use of PKCζ inhibitors as anti-inflammatory agents. We previously reported a series of 1,3,5-trisubstituted pyrazolines as potent and selective allosteric inhibitors of PKCζ; in that series of compounds, the phenolic OH at the 5-phenyl was essential for binding to the PKCζ PIF pocket. In

  人们对蛋白激酶 Czeta (PKC z) 在 NF-κB 激活中的重要作用以及 PKC z 抑制剂作为抗炎剂的潜在用途有了更多的了解。我们之前报道了一系列 1,3,5-三取代吡唑啉作为 PKCδ 的有效和选择性变构抑制剂；在该系列化合物中，5-苯基处的酚 OH 对于与 PKC z PIF 口袋的结合至关重要。在本研究中，我们令人惊讶地发现，用卤素取代它并同时将 OH 移至 3-苯基仍然会产生活性化合物。本文提出了此类化合物的扩展，具有新的重点库，其中 5-苯基处的酚羟基（据报道是活性的不可替代特征）被移至 3-苯基并被卤素取代。这组新化合物保持了相同水平的针对 PKCζ 的效力和针对 PKC 同工型的选择性，但针对 PIF 口袋突变体 PKCζ[Val297Leu] 的效力降低。值得注意的是，关键功能组的重新定位导致细胞效力显着增强。最有效的新型 PKC z 抑制剂之一2h能够抑制 RAW
• Antimalarial Alkoxylated and Hydroxylated Chalones:  Structure−Activity Relationship Analysis
  作者：Mei Liu、Prapon Wilairat、Mei-Lin Go

  DOI：10.1021/jm0101747

  日期：2001.12.1

  among the active compounds. Hydroxylated chalcones were less active than the corresponding alkoxylated analogues. When evaluated in vivo, 8 and 208 were comparable to chloroquine in extending the lifespan of infected mice. Multivariate data analysis showed that in vitro activity was mainly determined by the properties of ring B. Quantitative structure-activity relationship models with satisfactory predictive

  合成在环B上具有2'，3'，4'-三甲氧基，2'，4'-二甲氧基，4'-甲氧基，4'-乙氧基，2'，4'-二羟基和4'-羟基的邻苯二甲酰并在[3H]次黄嘌呤摄取测定中针对恶性疟原虫（K1）进行了体外评估。另一个环A是具有不同亲脂性的给电子或吸电子取代基的喹啉，吡啶，萘或苯环。三甲氧基6和27，二甲氧基7，8，29和甲氧基31类似物具有良好的体外活性（IC（50）<5 microM）。在活性化合物中很好地代表了3-喹啉基环A衍生物。羟基查耳酮的活性低于相应的烷氧基化类似物。在体内评估时，8和208在延长被感染小鼠的寿命方面与氯喹相当。多变量数据分析表明，体外活性主要取决于环B的特性。使用对潜在结构的投影，获得了各种B环查耳酮具有令人满意的预测能力的定量构效关系模型。提出了一个具有良好可预测性的模型，用于19个活动查尔肯。尺寸和疏水性被确定为关键参数。
• A FACILE ONE-POT SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF AZIRIDINES AND THIAZINES FROM 1,3-DIARYLPROP-2-ENONES
  作者：H. M. F. Madkour、M. A. I. Salem、E. A. Soliman、N. F. H. Mahmoud

  DOI：10.1080/10426500108040582

  日期：2001.3.1

  Abstract The title compounds 1a,b as examples for acyclic alkenones were utilized for the synthesis of some heterocycles namely, thiazines 2a,b and 3a-d, pyrimidines 4a,b. aziridines 7a,b. The unexpected tribromides 8a,b, obtained from bromination of 1a,b, were readily used to afford the pyrazoles 9a,b and isoxazoles 10 a,b. Biological screening of some selective synthesised compounds was determined

  摘要 标题化合物 1a、b 作为无环烯酮的实例用于合成一些杂环，即噻嗪 2a、b 和 3a-d、嘧啶 4a、b。氮丙啶 7a,b。从 1a、b 的溴化获得的意外三溴化物 8a、b 很容易用于提供吡唑 9a、b 和异恶唑 10a、b。使用革兰氏阴性和革兰氏阳性细菌菌株在体外确定了一些选择性合成化​​合物的生物学筛选。
• Antiproliferative properties of piperidinylchalcones
  作者：Xiaoling Liu、Mei-Lin Go

  DOI：10.1016/j.bmc.2005.08.006

  日期：2006.1

  Methoxylated chalcones bearing N-methylpiperidinyl substituents oil ring A inhibited the growth of human tumour cell lines (MCF, HCT 116, and Jurkat) at IC50 values or < 5 mu M. Investigations oil a representative member (12) showed that antiproliferative activity was linked to the disruption of the cell cycle at G1 and G2/M phases. The effect was concentration dependent and was evident at the approximate IC50 of 12. Down regulation of cell cycle regulatory components (CDK4, cyclin B, E2F, and phosphorylated Rb) were observed under similar conditions. Methoxylated chalconcs without the piperidinyl substituent were found to exert equally potent and selective antiproliferative activity against HCT 116 tumour cells but did not interfere with cell cycle progression at their IC50 concentrations. The presence of the piperidinyl substituent in the chalcone template is proposed to lend specificity to the mechanism of antiproliferative activity, in addition to promoting a more desirable physicochemical profile. (c) 2005 Elsevier Ltd. All rights reserved.
• Investigation of chalcones and benzochalcones as inhibitors of breast cancer resistance protein
  作者：Kapil Juvale、Veronika F.S. Pape、Michael Wiese

  DOI：10.1016/j.bmc.2011.10.074

  日期：2012.1

  Breast cancer resistance protein (BCRP/ABCG2) belongs to the ATP binding cassette family of transport proteins. BCRP has been found to confer multidrug resistance in cancer cells. A strategy to overcome resistance due to BCRP overexpression is the investigation of potent and specific BCRP inhibitors. The aim of the current study was to investigate different multi-substituted chalcones for their BCRP inhibition. We synthesized chalcones and benzochalcones with different substituents (viz. OH, OCH3, Cl) on ring A and B of the chalcone structure. All synthesized compounds were tested by Hoechst 33342 accumulation assay to determine inhibitory activity in MCF-7 MX and MDCK cells expressing BCRP. The compounds were also screened for their P-glycoprotein (P-gp) and Multidrug resistance-associated protein 1 (MRP1) inhibitory activity in the calcein AM accumulation assay and were found to be selective towards inhibition of BCRP. Substituents at position 20 and 40 on chalcone ring A were found to be essential for activity; additionally there was a great influence of substituents on ring B. Presence of 3,4-dimethoxy substitution on ring B was found to be optimal, while presence of 2- and 4-chloro substitution also showed a positive effect on BCRP inhibition. (C) 2011 Elsevier Ltd. All rights reserved.