2-(4-(benzyloxy)-3-methoxyphenyl)acetyl chloride | 54313-35-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-(benzyloxy)-3-methoxyphenyl)acetyl chloride
• 英文别名: 2-[4-(benzyloxy)-3-methoxyphenyl]acetyl chloride；(4-Benzyloxy-3-methoxy-phenyl)-acetyl chloride；4-benzyloxy-3-methoxyphenylacetyl chloride；2-(3-methoxy-4-phenylmethoxyphenyl)acetyl chloride
• CAS: 54313-35-8
• 化学式: C₁₆H₁₅ClO₃
• 分子量: 290.746
• InChiKey: VZASNANMUPXMRV-UHFFFAOYSA-N

物化性质

• 沸点：
  411.3±40.0 °C(Predicted)
• 密度：
  1.214±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  2-(4-(benzyloxy)-3-methoxyphenyl)acetyl chloride 在 盐酸 、 sodium carbonate 、 三氯氧磷 作用下， 以 乙醚 、 乙醇 、 水 、 乙腈 为溶剂， 反应 4.58h， 生成 4'-羟基罂粟碱
  参考文献：
  名称：

  Synthesis and in vitro evaluation of new analogues as inhibitors for phosphodiesterase 10A

  摘要：

  A series of analogues were synthesized by optimizing the structure of papaverine. The in vitro PDE10A binding affinity (IC50) values for these new analogues were measured; for compounds that have IC50 value less than 60 nM for PDE10A, the binding affinities (IC50 value) for PDE3A and PDE3B were tested. Of these analogues, compounds 6a, 6b, 6n, 8b, 8c and 11 displayed relatively higher PDE10A potency with IC50 value in the range of 28-60 nM. The most potent compound 1-(4-(2-(2-fluoroethoxy)ethoxy)-3-methoxybenzyl)-6,7-dimethoxyisoquinoline (8c) has the IC50 value of 28 +/- 1.2 nM for PDE10A, 2200 +/- 437 nM for PDE3A and 2520 +/- 210 nM for PDE3B. Compared to papaverine, compound 8c displayed similar PDE10A potency but improved selectivity to PDE10A versus PDE3A and PDE3B. To identify high potent PDE10A inhibitor, further optimization of the structures of these analogues is necessary. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.072
• 作为产物：
  描述：

  高香草酸 在 氢氧化钾 、 氯化亚砜 、 sodium 作用下， 以 甲醇 为溶剂， 生成 2-(4-(benzyloxy)-3-methoxyphenyl)acetyl chloride
  参考文献：
  名称：

  Horn; Dijkstra; Mulder, European Journal of Medicinal Chemistry, 1981, vol. 16, # 5, p. 469 - 472

  摘要：

  DOI：

文献信息

• Substituted Isoquinolinones and Quinazolinones
  申请人：BERGHAUSEN Joerg

  公开号：US20110230457A1

  公开（公告）日：2011-09-22

  The invention relates to substituted nitrogen containing bicyclic heterocycles of the formula (I) wherein Z is CH 2 or N—R 4 and X, R 1 , R 2 , R 4 , R 6 , R 7 and n are as defined in the description. Such compounds are suitable for the treatment of a disorder or disease which is mediated by the activity of MDM2 and/or MDM4, or variants thereof.

  这项发明涉及公式（I）中的取代氮含有的双环杂环化合物，其中Z为CH2或N—R4，X、R1、R2、R4、R6、R7和n的定义如描述中所述。这类化合物适用于治疗由MDM2和/或MDM4的活性介导的疾病或疾病变体。
• Biosynthesis. Part 24. Speculative incorporation experiments with 1-benzylisoquinolines and a logical approach via C₆–C₂and C₆–C₃precursors to the biosynthesis of hasubanonine and protostephanine
  作者：Alan R. Battersby、Raymond C. F. Jones、Rymantas Kazlauskas、Craig W. Thornber、Somsak Ruchirawat、James Staunton

  DOI：10.1039/p19810002016

  日期：——

  Many possible 1-benzyltetrahydroisoquinolines have been examined as possible advanced precursors of the alkaloids hasubanonine (1) and protostephanine (2) in Stephania japonica plants, but none was incorporated significantly. Administration of various precursor molecules having only one aromatic ring, such as tyrosine, has demonstrated that both alkaloids are derived from two different C6–C2 biogenetic

  已经研究了许多可能的1-苄基四氢异喹啉类化合物，它们是Stephania japonica植物中生物碱hasubanonine（1）和protostephanine（2）的可能的高级前体，但没有明显掺入。施用仅具有一个芳香环的各种前体分子（例如酪氨酸）已证明这两种生物碱均来自两个不同的C 6 -C 2生物遗传单位。随后无法进一步引入1-苄基四氢异喹啉和双苯乙胺，这表明（a）改性的1-苄基异喹啉或（b）三加氧的C 6 –C 2中间体建筑模块。设计用于检查第一种可能性的前体，例如1-苄基-3,4-二氢异喹啉或1-苄基-1-羧基四氢异喹啉，未合并到（1）和（2）中，而两个3'，4'，5'-掺入三氧化的2-苯基乙胺。这些发现允许进一步描述对生物碱（1）和（2）的后续前体的需求。
• Designing New Analogs for Streamlining the Structure of Cytotoxic Lamellarin Natural Products
  作者：Kassrin Tangdenpaisal、Rattana Worayuthakarn、Supatra Karnkla、Poonsakdi Ploypradith、Pakamas Intachote、Suchada Sengsai、Busakorn Saimanee、Somsak Ruchirawat、Montakarn Chittchang

  DOI：10.1002/asia.201403361

  日期：2015.4

  Despite the therapeutic potential of marine‐derived lamellarin natural products, their preclinical development has been hampered by their lipophilic nature, causing very poor aqueous solubility. In order to develop more drug‐like analogs, their structure was streamlined in this study from both the cytotoxic activity and lipophilicity standpoints. First, a modified total synthetic route was successfully

  尽管海洋来源的lamellarin天然产物具有治疗潜力，但其亲脂性质阻碍了它们的临床前开发，导致水溶性很差。为了开发更多类似药物的类似物，本研究从细胞毒性活性和亲脂性的角度简化了它们的结构。首先，成功设计了一条改良的总合成路线来构建59个系统设计的lamellarin类似物的文库，然后对其进行细胞毒性和log P测定。连同先前在我们实验室中合成的25种第一代薄片蛋白，对结构-活性和结构-亲脂性之间的关系进行了广泛的评估。我们的结果清楚地表明了层状蛋白骨架周围的其他结构要求，
• Facile and Divergent Synthesis of Lamellarins and Lactam-Containing Derivatives with Improved Drug Likeness and Biological Activities
  作者：Atiruj Theppawong、Poonsakdi Ploypradith、Pitak Chuawong、Somsak Ruchirawat、Montakarn Chittchang

  DOI：10.1002/asia.201500611

  日期：2015.12

  With the goal to improve the aqueous solubility of lamellarins, the lactone ring in their skeleton was replaced with a lactam moiety in azalamellarins. However, the reported synthetic route produced such derivatives in very low yields. Hence, this study focused on developing an efficient simplified total synthetic scheme that could furnish both azalamellarins and the parent lamellarins from the same pyrrole

  为了改善薄层蛋白的水溶性，其骨架中的内酯环被氮杂层蛋白中的内酰胺部分取代。然而，所报道的合成路线以非常低的产率产生了此类衍生物。因此，本研究着重于开发一种有效的简化的全合成方案，该方案可从相同的吡咯酯中间体中同时提供氮杂戊酰胺和母体薄片。随后的比较分析表明，引入的内酯-内酰胺替代使得这些分子的亲脂性降低，而它们的癌细胞毒性仍然与母体化合物相同。有趣的是，它们对多层面GSK-3β酶的抑制活性显着增强。
• Design, synthesis of a novel 4-<i>O</i>-methylsaucerneol analogue LXY7824 as potent HIF-1 inhibitor and anti-cancer agent
  作者：Xiao-Yu Liu、Xiao-Yu Li、Fei-Long Yang、Yan Li、Xiao-Zhen Jiao、Ping Xie

  DOI：10.1080/10286020.2018.1473386

  日期：2018.6.3

  important transcription factor for tumor survival, is an attractive target for anti-cancer treatment. Herein, we present the design and synthesis of LXY7824, a simplified analogue of 4-O-methylsaucerneol. In addition, its significant HIF-1 inhibitory activity and potent anti-cancer activity in vivo and in vitro were also reported.

  缺氧诱导因子1（HIF-1）是肿瘤存活的重要转录因子，是抗癌治疗的诱人靶标。在这里，我们介绍LXY7824的设计和合成，LXY7824是4- O-甲基紫杉醇的简化类似物。此外，还报道了其在体内和体外显着的HIF-1抑制活性和有效的抗癌活性。