3-(3,4,5-trimethoxyphenyl)propanoyl chloride | 66543-72-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(3,4,5-trimethoxyphenyl)propanoyl chloride
• 英文别名: 3-(3,4,5-trimethoxyphenyl)propionic acid chloride；3-(3',4',5'-trimethoxyphenyl)propionyl chloride
• CAS: 66543-72-4
• 化学式: C₁₂H₁₅ClO₄
• 分子量: 258.702
• InChiKey: IBSSQHOLZVHSAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3,4,5-trimethoxyphenyl)propanoyl chloride 在 一水合肼 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 N-(6-hydrazino-6-oxohexyl)-3-(3,4,5-trimethoxyphenyl)propanamide
  参考文献：
  名称：

  Novel Heterobivalent Tacrine Derivatives as Cholinesterase Inhibitors with Notable Selectivity Toward Butyrylcholinesterase

  摘要：

  Two series of novel heterobivalent tacrine derivatives were synthesized. A trimethoxy substituted benzene was linked to the tacrine moiety by a hydrazide-based linker. The compounds were evaluated as cholinesterase inhibitors, and trimethoxybenzoic acid derivatives with 11- or 12-atom spacers were the most potent inhibitors of human acetylcholinesterase. The inhibitors showed a surprising selectivity toward human butyrylcholinesterase, where several trimethoxyphenylpropionic acid derivatives had IC50 values less than 250 mu M.

  DOI：

  10.1021/jm060742o
• 作为产物：
  描述：

  3-(3,4,5-三甲氧基苯基)丙酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 3-(3,4,5-trimethoxyphenyl)propanoyl chloride
  参考文献：
  名称：

  cenocladamide类似物的设计与合成及其对乳腺癌细胞系的评估† ‡

  摘要：

  这项工作描述了生物碱倍半酰胺的完整合成和九个结构类似物的简明文库，旨在评估它们对乳腺癌细胞系MDA-MB-231的评价。在一组七个乳腺癌细胞系和两个非致瘤细胞系中也评估了最有前途的化合物（3； IC 50 = 6.6μM）。我们进一步对类似物3的作用机理进行了初步研究，与Cenocladamide相比，该类似物3没有内环双键。本研究提出了具有令人感兴趣的细胞毒性活性的倍生酰胺类似物的发现，这对于进一步优化用于乳腺癌治疗的新化学治疗剂可能是有用的。

  DOI：

  10.1039/c6md00577b

文献信息

• Controlled and Chemoselective Reduction of Secondary Amides
  作者：Guillaume Pelletier、William S. Bechara、André B. Charette

  DOI：10.1021/ja105194s

  日期：2010.9.22

  presence of 2-fluoropyridine. The electrophilic activated amide can then be reduced to the corresponding iminium using triethylsilane, a cheap, rather inert, and commercially available reagent. Imines can be isolated after a basic workup or readily transformed to the aldehydes following an acidic workup. The amine moiety can be accessed via a sequential reductive amination by the addition of silane and

  该通讯描述了一种不含金属的方法，该方法涉及在环境压力和温度下以良好至极好的收率将仲酰胺有效且受控地还原为亚胺、醛和胺。该方法包括在 2-氟吡啶存在下用三氟甲磺酸酐对仲酰胺进行化学选择性活化。然后可以使用三乙基硅烷（一种廉价、惰性且可商购的试剂）将亲电活化的酰胺还原为相应的亚胺鎓。亚胺可以在碱性处理后分离，也可以在酸性处理后容易地转化为醛。通过在一锅反应中加入硅烷和 Hantzsch 酯氢化物，可以通过顺序还原胺化获得胺部分。而且，
• [EN] NOVEL COMPOUNDS USEFUL AS S100-INHIBITORS<br/>[FR] NOUVEAUX COMPOSÉS UTILES EN TANT QU'INHIBITEURS DE S100
  申请人：ACTIVE BIOTECH AB

  公开号：WO2015177367A1

  公开（公告）日：2015-11-26

  A compound of formula (I) or a pharmaceutically acceptable salt thereof and a pharmaceutical composition comprising the compound. The compound is an inhibitor of interactions between S100A9 and interaction partners such as RAGE, TLR4 and EMMPRIN and as such is useful in the treatment of disorders such as cancer, autoimmune disorders, inflammatory disorders and neurodegenerative disorders.

  式（I）的化合物或其药用盐以及包含该化合物的药物组合物。该化合物是S100A9与相互作用伙伴（如RAGE、TLR4和EMMPRIN）之间相互作用的抑制剂，因此在治疗癌症、自身免疫性疾病、炎症性疾病和神经退行性疾病等疾病方面是有用的。
• Synthesis of Difluoromethyl Ketones from Weinreb Amides, and Tandem Addition/Cyclization of <i>o</i> -Alkynylaryl Weinreb Amides
  作者：Jongkonporn Phetcharawetch、Nolan M. Betterley、Darunee Soorukram、Manat Pohmakotr、Vichai Reutrakul、Chutima Kuhakarn

  DOI：10.1002/ejoc.201701322

  日期：2017.12.15

  [Difluoro(phenylsulfanyl)methyl]trimethylsilane (PhSCF2SiMe3) underwent a fluoride-induced nucleophilic addition to the carbonyl group of Weinreb amides to provide the corresponding difluoro(phenylsulfanyl)methyl ketones. These were converted into difluoromethyl ketones through selective reductive cleavage of the phenylsulfanyl group. The reaction of o-alkynyl Weinreb amides derived from benzoic acid derivatives resulted

  [二氟（苯硫基）甲基]三甲基硅烷（PhSCF2SiMe3）与Weinreb酰胺的羰基发生氟化物诱导的亲核加成反应，得到相应的二氟（苯硫基）甲基酮。它们通过苯硫基的选择性还原裂解转化为二氟甲基酮。衍生自苯甲酸衍生物的邻炔基 Weinreb 酰胺的反应导致通过 5-exo-dig 环化形成环化产物。
• Description anti-mitotic agents which inhibit tubulin polymerization
  申请人：Baylor University

  公开号：US06350777B2

  公开（公告）日：2002-02-26

  Methoxy and ethoxy substituted 3-aroyl-2-arylbenzo[b]thiophenes and benzo[b]thiophene analogues are described for use in inhibiting tubulin polymerization. The compounds' use for treating tumor cells is also described. Additional aspects described here are certain diaryl ether benzo[b]thiophene derivatives. Also described are particular analogs derived from dihydronaphthalene which have proven particularly effective. Certain new benzofuran analogs are described, as well as certain sulfur oxide benzo[b]thiophene analogs. Important compounds described herein include the first nitrogen-containing derivatives of combretastatin. These include nitro, amino and azide combrdtastatin derivatives.

  甲基氧基和乙氧基取代的3-酰基-2-芳基苯并[b]噻吩及其类似物被描述用于抑制微管蛋白聚合。这些化合物用于治疗肿瘤细胞的方法也进行了描述。 此外，这里还描述了某些二芳基醚苯并[b]噻吩衍生物。还描述了来自二氢萘的特定类似物，这些类似物已被证明特别有效。描述了一些新的苯并呋喃类似物，以及某些硫氧化物苯并[b]噻吩类似物。 本文描述的重要化合物包括含有氮的康布雷他汀衍生物的首个例子。这些包括硝基、氨基和叠氮化物康布雷他汀衍生物。
• Activity-based protein profiling reveals GSTO1 as the covalent target of piperlongumine and a promising target for combination therapy for cancer
  作者：Li Li、Yue Zhao、Ran Cao、Lin Li、Gaihong Cai、Jiaojiao Li、Xiangbing Qi、She Chen、Zhiyuan Zhang

  DOI：10.1039/c9cc00917e

  日期：——

  Through ABPP, piperlongumine was identified to induce cancer cell death by covalently binding and inhibiting GSTO1 and has a broad spectrum synergistic effect with other anti-cancer agents.

  通过ABPP，已确定piperlongumine通过共价结合和抑制GSTO1诱导癌细胞死亡，并与其他抗癌药物具有广谱协同作用。