2-溴-4-甲酰基-6-甲氧基乙酸苯酯 | 308088-29-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 中文名称: 2-溴-4-甲酰基-6-甲氧基乙酸苯酯
• 中文别名: 2-溴-4-甲酰-6-甲氧基乙酸苯酯
• 英文名称: 4-acetoxy-3-bromo-5-methoxybenzaldehyde
• 英文别名: 4-Acetoxy-3-brom-5-methoxy-benzaldehyd；2-bromo-4-formyl-6-methoxyphenyl acetate；(2-bromo-4-formyl-6-methoxyphenyl) acetate
• CAS: 308088-29-1
• 化学式: C₁₀H₉BrO₄
• mdl: MFCD02090077
• 分子量: 273.083
• InChiKey: SXSITNPVULYEFB-UHFFFAOYSA-N

物化性质

• 熔点：
  87 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2915390090

反应信息

• 作为反应物：
  描述：

  2-溴-4-甲酰基-6-甲氧基乙酸苯酯 在 硝酸 作用下， 生成 4-acetoxy-5-bromo-3-methoxy-2-nitro-benzaldehyde
  参考文献：
  名称：

  芳香族亲电子取代的立体电子控制。能量独立共振的重要性

  摘要：

  在极化芳香族化合物的亲电子取代中观察到意外的区域化学现象被解释为是通过过渡态发生的，该过渡态最类似于最低能量的价键芳香族共振形式。电攻击邻的芳醚或酯被建议发生反-antiperi平面到非键，共面的氧轨道，因此S-顺式到该取代基，得到所观察到的低的邻位/对位，因为引导散装的比率团体。

  DOI：

  10.1039/c39820001333
• 作为产物：
  描述：

  5-溴香兰素 、 乙酸酐 生成 2-溴-4-甲酰基-6-甲氧基乙酸苯酯
  参考文献：
  名称：

  147.天然酚醛树脂的成分。第十九部分。阿魏酸的氧化

  摘要：

  DOI：

  10.1039/jr9440000535

文献信息

• Substituted 4-aryl-4h-pyrrolo[2,3-h]chromenes and analogs as activators of caspases and inducers of apoptosis and the use thereof
  申请人：Cai Xiong Sui

  公开号：US20060104998A1

  公开（公告）日：2006-05-18

  The present invention is directed to substituted 4H-chromenes and analogs thereof, represented by the Formula (I): wherein R 1 , R 3 -R 5 , A, D, Y and Z are defined herein. The present invention also relates to the discovery that compounds having Formula (I) are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention can be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及被代替的4H-香豆素及其类似物，由式（I）表示：其中R1，R3-R5，A，D，Y和Z在此处定义。本发明还涉及发现具有式（I）的化合物是caspase的激活剂和凋亡诱导剂。因此，本发明的caspase激活剂和凋亡诱导剂可用于诱导在发生细胞不受控制生长和异常细胞扩散的各种临床状况中的细胞死亡。
• Structural simplification of bioactive natural products with multicomponent synthesis: Dihydropyridopyrazole analogues of podophyllotoxin
  作者：Igor V. Magedov、Madhuri Manpadi、Elena Rozhkova、Nikolai M. Przheval’skii、Snezna Rogelj、Scott T. Shors、Wim F.A. Steelant、Severine Van slambrouck、Alexander Kornienko

  DOI：10.1016/j.bmcl.2006.11.095

  日期：2007.3

  aliphatic aldehydes leads to the formation of dihydropyridopyrazole analogues of a cytotoxic lignan podophyllotoxin. This new heterocyclic scaffold-based library allows a drastic reduction of the structural complexity of the natural product with the retention of its potent cytotoxic properties. Similarly to podophyllotoxin, the presented analogues induce apoptosis in Jurkat cells.

  5-氨基-3-甲基吡唑，tetronic酸和各种芳香族，杂芳香族和脂肪族醛的三组分缩合导致细胞毒性木脂多糖鬼臼毒素的二氢吡啶并吡唑类似物的形成。这个新的基于杂环支架的文库可以大大降低天然产物的结构复杂性，并保留其有效的细胞毒性。与鬼臼毒素相似，提出的类似物诱导Jurkat细胞凋亡。
• 10.1021/acs.jmedchem.3c02460
  作者：Zhang, Yiting、Li, Xiangqian、Liu, Fang、Bai, Xiaoyi、Liu, Xiaochun、Sun, Hao、Gao, Chenxia、Lin, Yuxi、Xing, Pan、Zhu, Jiqiang、Liu, Ruihua、Wang, Zemin、Dai, Jiajia、Shi, Dayong

  DOI：10.1021/acs.jmedchem.3c02460

  日期：——

  Designing selective PARP-1 inhibitors has become a new strategy for anticancer drug development. By sequence comparison of PARP-1 and PARP-2, we identified a possible selective site (S site) consisting of several different amino acid residues of α-5 helix and D-loop. Targeting this S site, 140 compounds were designed, synthesized, and characterized for their anticancer activities and mechanisms. Compound

  设计选择性PARP-1抑制剂已成为抗癌药物开发的新策略。通过对PARP-1和PARP-2的序列比较，我们鉴定了一个可能的选择性位点（S位点），该位点由α-5螺旋和D环的几个不同氨基酸残基组成。针对该 S 位点，设计、合成了 140 种化合物，并对其抗癌活性和机制进行了表征。化合物I16显示出最高的 PARP-1 酶抑制活性 (IC 50 = 12.38 ± 1.33 nM) 和优于 PARP-2 的最佳选择性指数 (SI = 155.74)。口服I16 （25 mg/kg）对Hela和SK-OV-3肿瘤细胞异种移植模型显示出较高的抑制率，均高于口服阳性药物Olaparib（50 mg/kg）。此外， I16具有出色的安全性，高口服剂量时没有明显毒性。这些发现为开发安全、高效和高选择性的 PARP-1 抑制剂提供了新颖的设计策略和化学型。
• Discovery of 4-Aryl-4<i>H</i>-chromenes as a New Series of Apoptosis Inducers Using a Cell- and Caspase-Based High-Throughput Screening Assay. 3. Structure−Activity Relationships of Fused Rings at the 7,8-Positions
  作者：William Kemnitzer、John Drewe、Songchun Jiang、Hong Zhang、Jianghong Zhao、Candace Crogan-Grundy、Lifen Xu、Serge Lamothe、Henriette Gourdeau、Réal Denis、Ben Tseng、Shailaja Kasibhatla、Sui Xiong Cai

  DOI：10.1021/jm070216c

  日期：2007.6.1

  As a continuation of our efforts to discover and develop the apoptosis-inducing 4-aryl-4H-chromenes as novel anticancer agents, we explored the SAR of fused rings at the 7,8-positions. It was found that a five-member aromatic ring, such as pyrrolo with nitrogen at either the 7- or 9-position, is preferred. A six-member aromatic ring, such as benzo or pyrido, also led to potent compounds. The SAR of the 4-aryl group was found to be similar for chromenes with a fused ring at the 7,8-positions. These compounds were found to inhibit tubulin polymerization, indicating that cyclization of the 7,8-positions into a ring does not change the mechanism of action. Compound 2h was identified to be a highly potent apoptosis inducer with an EC50 of 5 nM and a highly potent inhibitor of cell proliferation with a GI(50) of 8 nM in T47D cells.
• Thiosemicarbazones of Some Vanillin Derivatives
  作者：R. P. Perry

  DOI：10.1021/ja01642a073

  日期：1954.7