3,4-bis(methoxymethoxy)benzoic acid | 149220-87-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4-bis(methoxymethoxy)benzoic acid
• 英文别名: 3,4-di(methoxymethoxy)benzoic acid
• CAS: 149220-87-1
• 化学式: C₁₁H₁₄O₆
• 分子量: 242.229
• InChiKey: RPXJIJXOAQZKFO-UHFFFAOYSA-N

物化性质

• 沸点：
  380.4±42.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4-bis(methoxymethoxy)benzoic acid 在 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 potassium carbonate 、 二乙胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 生成 [2-Bromo-4,5-bis(methoxymethoxy)phenyl] trifluoromethanesulfonate
  参考文献：
  名称：

  第一全合成和clusiparalicoline A的神经营养活性，异戊二烯化和从geranylated联芳基Clusia paralicola

  摘要：

  clusiparalicoline A的第一合成，从根分离的异戊二烯化和geranylated联苯化合物Clusia paralicola，一直通过将连续的钯催化的Stille和Suzuki反应的所有CC键的形成上的富电子的芳基实现溴化物和三氟甲磺酸。已经发现，在胎儿大鼠皮层神经元的原代培养物中，Clusiparalicoline A在1.0μM时表现出有效的神经突生长促进活性。

  DOI：

  10.1016/s0040-4039(02)01630-1
• 作为产物：
  描述：

  3,4-双(甲氧基甲氧基)苯甲醛 在 potassium hydrogencarbonate 、 间氯过氧苯甲酸 作用下， 生成 3,4-bis(methoxymethoxy)benzoic acid
  参考文献：
  名称：

  第一全合成和clusiparalicoline A的神经营养活性，异戊二烯化和从geranylated联芳基Clusia paralicola

  摘要：

  clusiparalicoline A的第一合成，从根分离的异戊二烯化和geranylated联苯化合物Clusia paralicola，一直通过将连续的钯催化的Stille和Suzuki反应的所有CC键的形成上的富电子的芳基实现溴化物和三氟甲磺酸。已经发现，在胎儿大鼠皮层神经元的原代培养物中，Clusiparalicoline A在1.0μM时表现出有效的神经突生长促进活性。

  DOI：

  10.1016/s0040-4039(02)01630-1

文献信息

• Syntheses of the Acridone Alkaloid Citrusinine-I and Its Derivatives.
  作者：Nobuharu KATO、Masanobu FUJITA、Ken-ichi FUJIMURA、Yoichi KAWASHIMA、Yukihiro NISHIYAMA

  DOI：10.1248/cpb.41.445

  日期：——

  Citrusinine-I (1), a naturally occurring acridone alkaloid with potent anitiviral activity, was synthesized for the first time, via a route involving Ulmann reaction, cyclization, and selective demethylation at the 1-position with boron trifluoride etherate and lithium bromide. 1, 5, 6-Trihydroxy-3-methoxy-9(10H)-acridone (2a) and 1, 5, 6-trihydroxy-3-methoxy-10-methyl-9(10H)-acridone (2b) were also synthesized.

  通过乌尔曼反应、环化以及用三氟化硼醚化物和溴化锂在 1 位进行选择性去甲基化的方法，首次合成了具有强效抗病毒活性的天然吖啶酮生物碱 Citrusinine-I（1）。此外，还合成了 1, 5, 6-三羟基-3-甲氧基-9(10H)-吖啶酮 (2a) 和 1, 5, 6-三羟基-3-甲氧基-10-甲基-9(10H)-吖啶酮 (2b)。
• NOVEL SULFONAMIDOMETHYLPHOSPHONATE INHIBITORS OF BETA-LACTAMASE
  申请人：Dininno Frank

  公开号：US20100317625A1

  公开（公告）日：2010-12-16

  This invention provides novel β-lactamase inhibitors of the aryl- and heteroaryl-sulfonamidomethylphosphonate monoester class. The compounds inhibit three classes of β-lactamases and synergize the antibacterial effects of β-lactam antibiotics (e.g., imipenem and ceftazimdime) against those micro-organisms normally resistant to the β-lactam antibiotics as a result of the presence of the β-lactamases.

  本发明提供了一种新型的苯基和杂环基磺酰胺甲基膦酸酯类β-内酰胺酶抑制剂。这些化合物可以抑制三类β-内酰胺酶，并且可以协同β-内酰胺类抗生素（如亚胺培南和头孢他啶）的抗菌效果，对那些由于β-内酰胺酶的存在而正常耐受β-内酰胺类抗生素的微生物产生抗菌作用。
• WO2007/139729
  申请人：——

  公开号：——

  公开（公告）日：——
• Antimicrobial effects of novel siderophores linked to β-lactam antibiotics
  作者：T Kline、M Fromhold、T.E McKennon、S Cai、J Treiberg、N Ihle、D Sherman、W Schwan、M.J Hickey、P Warrener、P.R Witte、L.L Brody、L Goltry、L.M Barker、S.U Anderson、S.K Tanaka、R.M Shawar、L.Y Nguyen、M Langhorne、A Bigelow、L Embuscado、E Naeemi

  DOI：10.1016/s0968-0896(99)00261-8

  日期：2000.1

  As a strategy to increase the penetration of antibiotic drugs through the outer membrane of Gram-negative pathogens, facilitated transport through siderophore receptors has been frequently exploited. Hydroxamic acids, catechols, or very close isosteres of catechols, which are mimics of naturally occurring siderophores, have been used successfully as covalently linked escorting moieties, but a much wider diversity of iron binding motifs exists. This observation, coupled to the relative lack of specificity of siderophore receptors, prompted us to initiate a program to identify novel, noncatechol siderophoric structures. We screened over 300 compounds for their ability to (1) support growth in low iron medium of a Pseudomonas aeruginosa siderophore biosynthesis deletion mutant, or (2) compete with a bactericidal siderophore-antibiotic conjugate for siderophore receptor access. From these assays we identified a set of small molecules that fulfilled one or both of these criteria. We then synthesized these compounds with functional groups suitable for attachment to both monobactam and cephalosporin core structures. Siderophore-P-lactam conjugates then were tested against a panel of Escherichia coli, Pseudomonas aeruginosa, and Staphylococcus aureus strains. Although several of the resultant chimeric compounds had antimicrobial activity approaching that of ceftazidime, and most compounds demonstrated very potent activity against their cellular targets, only a single compound was obtained that had enhanced, siderophore-mediated antibacterial activity. Results with tonB mutants frequently showed increased rather than decreased susceptibilities, suggesting that multiple factors influenced the intracellular concentration of the drugs. (C) 2000 Elsevier Science Ltd. All rights reserved.
• [EN] NOVEL SULFONAMIDOMETHYLPHOSPHONATE INHIBITORS OF BETA-LACTAMASE<br/>[FR] NOUVEAUX INHIBITEURS DE BÊTA-LACTAMASES DE TYPE SULFONAMIDOMÉTHYLPHOSPHONATE
  申请人：MERCK & CO INC

  公开号：WO2007139729A1

  公开（公告）日：2007-12-06

  [EN] This invention provides novel ß-lactamase inhibitors of the aryl-and heteroaryl-sulfonamidomethylphosphonate monoester class. The compounds inhibit three classes of ß-lactamases and synergize the antibacterial effects of ß-lactam antibiotics (e.g., imipenem and ceftazimdime) against those micro-organisms normally resistant to the ß-lactam antibiotics as a result of the presence of the ß-lactamases. Formula (I) or a pro-drug or pharmaceutically acceptable salt thereof, wherein: W represents: Formula (II).
  [FR] La présente invention concerne de nouveaux inhibiteurs de ß-lactamases de la classe des monoesters d'aryl- et d'hétéroaryl-sulfonamidométhylphosphonate. Les composés inhibent trois classes de ß-lactamases et présentent des synergies avec les effets antibactériens des antibiotiques de type ß-lactame (par exemple imipenem et ceftazimdime) contre les micro-organismes qui sont habituellement résistants aux antibiotiques de type ß-lactame du fait de la présence de ß-lactamases. Formule (I) ou son promédicament ou son sel de qualité pharmaceutique, W représentant : Formule (II).