(E)-3-(2-bromo-4,5-dimethoxyphenyl)-1-phenylprop-2-en-1-one

• 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: (E)-3-(2-bromo-4,5-dimethoxyphenyl)-1-phenylprop-2-en-1-one
• 化学式: C₁₇H₁₅BrO₃
• 分子量: 347.208
• InChiKey: KEAFTOPWMBMQFJ-CMDGGOBGSA-N

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：

  (E)-3-(2-bromo-4,5-dimethoxyphenyl)-1-phenylprop-2-en-1-one 在 盐酸 、 溶剂黄146 、 sodium t-butanolate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 ethyl 3-acetamido-4-(2-bromo-4,5-dimethoxyphenyl)-6-phenyl-1,2,3-trihydro-2-pyridone-3-carboxylate
  参考文献：
  名称：

  3-Aryl β-carbolin-1-ones as a new class of potent inhibitors of tumor cell proliferation: synthesis and biological evaluation

  摘要：

  一种新颖的三步合成3-芳基β-卡巴啉-1-酮的方法已经开发。通过将乙酰氨基氰基乙酸乙酯与查尔酮进行迈克尔加成，高效引入了β-卡巴啉-1-酮中的两个氮原子。所需的吡啶酮和吲哚环分别通过水合盐酸-醋酸介导的分子内酮- nitrile环化以及铜(I)催化的分子内氨基的N-芳基化组合而成。目标化合物在抑制肿瘤细胞增殖方面显示出显著活性。

  DOI：

  10.1039/b412921k
• 作为产物：
  描述：

  2-溴苯乙酮 在 sodium hydroxide 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 20.0h， 生成 (E)-3-(2-bromo-4,5-dimethoxyphenyl)-1-phenylprop-2-en-1-one
  参考文献：
  名称：

  顺序一锅卡宾催化的分子内 Stetter 反应和酸介导的缩合：获得 π-扩展多环芳烃的杂原子类似物

  摘要：

  在这封信中，我们基于卡宾催化的分子内 Stetter 反应的设计，公开了一种简单有效的方法来获得各种菲 [9,10- b ] 呋喃和 1 H-二苯并 [ e , g ]吲哚衍生物通过一锅中的 Paal-Knorr 反应。这些化合物是一类含有氧/氮原子的 π 延伸多环芳烃 (PAH) 衍生物。所开发转化的实际效用在克级及其合成后转化上得到证明。

  DOI：

  10.1021/acs.orglett.2c02693

文献信息

• CuI catalyzed N-arylation of amide as a key step for the preparation of 3-aryl β-carbolin-1-ones
  作者：Shaozhong Wang、Jianwei Sun、Gang Yu、Xiaoyi Hu、Jun O Liu、Yuefei Hu

  DOI：10.1039/b406046f

  日期：——

  An expedient synthetic route for 3-aryl β-carbolin-1-ones was developed starting from ethyl acetamidocyanoacetate and chalcone derivatives. The five- and six-membered nitrogen-containing rings in the β-carbolin-1-ones were elaborated efficiently by an intramolecular ketone-nitrile annulation and an intramolecular N-arylation of amide respectively.

  一种便捷的合成路线已开发出用于合成3-芳基β-咔啉-1-酮，起始材料为乙基乙酰胺氰乙酸酯和查尔酮衍生物。β-咔啉-1-酮中的五元和六元含氮环通过分子内酮-氰基环化和分子内酰胺N-芳基化分别高效地构建。
• 찰콘 유도체를 포함하는 신장 보호용 조성물
  申请人：KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY 한국과학기술연구원(319980077518) BRN ▼209-82-03522

  公开号：KR20190050074A

  公开（公告）日：2019-05-10

  본 명세서는 찰콘 유도체를 포함하는 신장 보호용 조성물 또는 신장질환 개선용 조성물에 관한 것으로서, 본 명세서에 의한 화합물을 이용할 경우 약물 등에 의한 신독성으로부터 신장을 보호할 수 있어, 약물과 관련된 신장질환의 효과적 개선을 도모할 수 있으므로, 본 명세서를 활용하여 환자 치료 및 복지 분야에 있어서 큰 기여를 도모할 수 있을 것이다.

  该规范涉及包含钙调素诱导体的肾脏保护配方或肾脏疾病改善配方，通过使用本规范中的化合物，可以保护肾脏免受药物等的肾毒性，从而促进与药物相关的肾脏疾病的有效改善，因此利用本规范可以在患者治疗和福利领域做出重大贡献。
• Elucidation of protective effects of oxime derivatives against cisplatin-induced cytotoxicity in LLC-PK1 kidney cells
  作者：Dahae Lee、Sang Hyuk Lee、Heesu Lee、You‐Kyung Choi、Ki Sung Kang、Jae Wook Lee

  DOI：10.1016/j.bmcl.2022.129114

  日期：2023.1

  oxime derivatives against cisplatin-mediated cell death in LLC-PK1 porcine kidney epithelial cells. Treatment with compounds 161-A and 161-F improved cisplatin-mediated LLC-PK1 cell damage and increased cell viability by more than 80% of the control value when compared with that of cisplatin-treated cells. In addition, 161-A and 161-F reduced cisplatin-induced apoptosis. Analysis of the molecular mechanisms

  本研究旨在探讨肟衍生物对顺铂介导的 LLC-PK1 猪肾上皮细胞死亡的肾脏保护作用。与顺铂处理的细胞相比，用化合物161-A和161-F处理可改善顺铂介导的 LLC-PK1 细胞损伤，并使细胞活力提高超过对照值的 80%。此外，161-A和161-F减少了顺铂诱导的细胞凋亡。对这些化合物发挥作用的分子机制的分析表明，用161-A和161-B处理可抑制细胞外信号调节激酶 (ERK) 和 c-Jun N的蛋白表达顺铂处理的 LLC-PK1 细胞中的末端激酶 (JNK) 和裂解的 caspase-3。因此，这些发现提供了体外科学证据，证明肟衍生物可用作预防顺铂介导的肾毒性的药理学候选物。
• 2-Bromo-4,5-Dimethoxy Chalcone Inhibits Cisplatin-induced LLC-PK1 Kidney Cell Death
  作者：Dahae Lee、Heesu Lee、Ki Sung Kang、Jae Wook Lee

  DOI：10.1002/bkcs.11454

  日期：2018.5

  The kidney has various functions, including modulating blood pressure, balancing electrolytes, and controlling blood volume. Among these functions, extracting metabolic waste from blood plays an important role in kidney. 1,2 Additionally, kidney epithelial cells are vulnerable to the toxic effects of various chemical agents and medications. 3,4 Recently, cisplatin, an inorganic platinum-based chemotherapeutic agent, has been used to inhibit solid malignant tumors due to its high therapeutic potential. 5,6 However, continuous exposure to cisplatin can cause various significant side effects, such as bone marrow suppression, peripheral neuropathy, and nephrotoxicity. In particular, a single dose of cisplatin treatment can cause nephrotoxicity among one-third of patients.(7-9) Therefore, it has been suggested to develop medication for cisplatin-induced nephrotoxicity.
• 3-Aryl β-carbolin-1-ones as a new class of potent inhibitors of tumor cell proliferation: synthesis and biological evaluation
  作者：Shaozhong Wang、Yanmei Dong、Xinyan Wang、Xiaoyi Hu、Jun O Liu、Yuefei Hu

  DOI：10.1039/b412921k

  日期：——

  A novel three-step synthesis of 3-aryl β-carbolin-1-ones from non-indole starting materials has been developed. The two nitrogen atoms in β-carbolin-1-one were introduced efficiently by Michael addition of ethyl acetamidocyanoacetate to chalcone. The desired pyridone and indole rings were assembled by an intramolecular ketone–nitrile annulation mediated by aqueous HCl–HOAc and a Cu(I)-catalyzed intramolecular N-arylation of the amide, respectively. The target compounds were found to possess significant activity against tumor cell proliferaton.

  一种新颖的三步合成3-芳基β-卡巴啉-1-酮的方法已经开发。通过将乙酰氨基氰基乙酸乙酯与查尔酮进行迈克尔加成，高效引入了β-卡巴啉-1-酮中的两个氮原子。所需的吡啶酮和吲哚环分别通过水合盐酸-醋酸介导的分子内酮- nitrile环化以及铜(I)催化的分子内氨基的N-芳基化组合而成。目标化合物在抑制肿瘤细胞增殖方面显示出显著活性。