methyl 2,2-diphenylbenzo[d][1,3]dioxole-4-carboxylate | 72553-33-4

• 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: methyl 2,2-diphenylbenzo[d][1,3]dioxole-4-carboxylate
• 英文别名: Methyl 2,2-diphenyl-2H-1,3-benzodioxole-4-carboxylate；methyl 2,2-diphenyl-1,3-benzodioxole-4-carboxylate
• CAS: 72553-33-4
• 化学式: C₂₁H₁₆O₄
• 分子量: 332.356
• InChiKey: QOUVARWAPFXPFU-UHFFFAOYSA-N

物化性质

• 沸点：
  473.0±45.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  methyl 2,2-diphenylbenzo[d][1,3]dioxole-4-carboxylate 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 31.75h， 生成 N-(苄氧羰基)-1,4-丁二胺
  参考文献：
  名称：

  Platform to Discover Protease-Activated Antibiotics and Application to Siderophore–Antibiotic Conjugates

  摘要：

  Here we present a platform for discovery of protease-activated prodrugs and apply it to antibiotics that target Gram-negative bacteria. Because cleavable linkers for prodrugs had not been developed for bacterial proteases, we used substrate phage to discover substrates for proteases found in the bacterial periplasm. Rather than focusing on a single protease, we used a periplasmic extract of E. coli to find sequences with the greatest susceptibility to the endogenous mixture of periplasmic proteases. Using a fluorescence assay, candidate sequences were evaluated to identify substrates that release native amine-containing payloads. We next designed conjugates consisting of (1) an N-terminal siderophore to facilitate uptake, (2) a protease-cleavable linker, and (3) an amine-containing antibiotic. Using this strategy, we converted daptomycin-which by itself is active only against Gram-positive bacteria-into an antibiotic capable of targeting Gram-negative Acinetobacter species. We similarly demonstrated siderophore-facilitated delivery of oxazolidinone and macrolide antibiotics into a number of Gram-negative species. These results illustrate this platform's utility for development of protease-activated prodrugs, including Trojan horse antibiotics.

  DOI：

  10.1021/jacs.0c06987
• 作为产物：
  描述：

  苯甲酸,二羟基- 在 氯化亚砜 、 三乙胺 作用下， 以 neat (no solvent) 为溶剂， 反应 16.0h， 生成 methyl 2,2-diphenylbenzo[d][1,3]dioxole-4-carboxylate
  参考文献：
  名称：

  Diphenyl-benzo[1,3]dioxole-4-carboxylic acid pentafluorophenyl ester: a convenient catechol precursor in the synthesis of siderophore vectors suitable for antibiotic Trojan horse strategies

  摘要：

  儿茶酚是许多金属螯合物的成分，包括由微生物分泌的天然存在的铁(III)螯合剂——侧胞素。儿茶酚衍生物在有机介质中溶解性差，合成含儿茶酚的分子需要使用具有更好有机溶解性的保护儿茶酚前体。因此，我们开发了2,2-二苯基-苯并[1,3]二噁烷-4-羧酸五氟苯酯。这种活化酯可以与一种氨基功能化的骨架反应，生成在二苯基-苯并二噁烷基团形式下保护的儿茶酚功能团。合成结束时，儿茶酚可以通过三氟乙酸（TFA）去保护。该策略用于合成两种带有末端炔基扩展的儿茶酚化合物。这两种化合物被证明能促进大肠杆菌和铜绿假单胞菌对铁的摄取。这两种化合物适合用作抗生素特洛伊木马方法中的载体，因为它们可以通过胡根偶极体1,3-环加成与叠氮功能化抗生素结合。

  DOI：

  10.1039/c3ob41990h

文献信息

• New COMT inhibitors for the treatment of depression and impaired cognition
  申请人：Diederich Francois

  公开号：US20050137162A1

  公开（公告）日：2005-06-23

  The present invention relates to compounds of formula I wherein R 1 is as defined in the specification and to esters thereof which are hydrolyzable under physiological conditions and to the pharmaceutically acceptable salts thereof. The compounds of the invention are inhibitors of COMT and, thus, are useful for the treatment of diseases for which COMT inhibition is beneficial. The invention further relates to the treatment, control, or prevention of diseases such as depression, schizophrenia, Parkinson's disease, and to improve cognition.

  本发明涉及以下式I的化合物 其中R 1 如规范中定义 以及在生理条件下可水解的酯及其药用可接受的盐。本发明的化合物是COMT的抑制剂，因此对于COMT抑制有益的疾病的治疗是有用的。本发明还涉及治疗、控制或预防抑郁症、精神分裂症、帕金森病以及改善认知的疾病。
• Diphenyl-benzo[1,3]dioxole-4-carboxylic acid pentafluorophenyl ester: a convenient catechol precursor in the synthesis of siderophore vectors suitable for antibiotic Trojan horse strategies
  作者：Etienne Baco、Françoise Hoegy、Isabelle J. Schalk、Gaëtan L. A. Mislin

  DOI：10.1039/c3ob41990h

  日期：——

  Catechols are components of many metal-chelating compounds, including siderophores that are naturally occurring iron(III) chelators excreted by microorganisms. Catechol derivatives are poorly soluble in organic media and the synthesis of catechol-containing molecules requires the use of protected catechol precursors with improved organic solubility. We therefore developed 2,2-diphenyl-benzo[1,3]dioxole-4-carboxylic acid pentafluorophenyl ester. This activated ester reacts with an amine functionalized scaffold to generate chelators in which the catechol functions are protected in the form of diphenyl-benzodioxole moieties. The catechol can subsequently be deprotected, at the end of the synthesis, with trifluoroacetic acid (TFA). This strategy was applied to the synthesis of two catechol compounds functionalized with a terminal propargyl extension. These two compounds were shown to promote iron uptake in Escherichia coli and Pseudomonas aeruginosa. These two compounds are suitable for use as vectors in antibiotic Trojan horse approaches, as they could be conjugated with azide-functionalized antibiotics using the Huisgen dipolar 1,3-cycloaddition.

  儿茶酚是许多金属螯合物的成分，包括由微生物分泌的天然存在的铁(III)螯合剂——侧胞素。儿茶酚衍生物在有机介质中溶解性差，合成含儿茶酚的分子需要使用具有更好有机溶解性的保护儿茶酚前体。因此，我们开发了2,2-二苯基-苯并[1,3]二噁烷-4-羧酸五氟苯酯。这种活化酯可以与一种氨基功能化的骨架反应，生成在二苯基-苯并二噁烷基团形式下保护的儿茶酚功能团。合成结束时，儿茶酚可以通过三氟乙酸（TFA）去保护。该策略用于合成两种带有末端炔基扩展的儿茶酚化合物。这两种化合物被证明能促进大肠杆菌和铜绿假单胞菌对铁的摄取。这两种化合物适合用作抗生素特洛伊木马方法中的载体，因为它们可以通过胡根偶极体1,3-环加成与叠氮功能化抗生素结合。
• New polycyclic β-lactams. Synthesis of 2a,3-dihydroazeto[1,2-a]quinoline-1,4(2H)-diones, structural analogues of the carbacephalosporin antibiotics
  作者：Mario D. Bachi、Joseph Klein

  DOI：10.1039/p19830001925

  日期：——

  dihydroxydihydroazeto[1,2-a]quinoline-1,4(2H)-diones (1). The synthesis involved, as a key step, the completion of the polycyclic β-lactam system by a modified Bischler–Napieralski reaction. It was illustrated by the synthesis of (±)-7,8-dihydroxy-3,3-dimethyl-2-phenoxyacetamido-2a,3-dihydroazeto[1,2-a]quinoline-1,4(2H)-dione (20), which is structurally related to the carbacephalosporin antibiotics.

  已经开发了一种制备二羟基二氢氮杂[1,2 - a ]喹啉-1,4（2H）-二酮（1）的方法。作为关键步骤，合成过程涉及通过修饰的Bischler-Napieralski反应完成多环β-内酰胺系统。通过（±）-7,8-二羟基-3,3-二甲基-2-苯氧基乙酰胺基-2a，3-二氢氮杂并[1,2 - a ]喹啉-1,4（2 H）-二酮的合成说明了这一点。（20），其在结构上与氨基头孢菌素抗生素有关。
• [EN] CHELATING PLATFORM FOR DELIVERY OF RADIONUCLIDES<br/>[FR] PLATE-FORME DE CHÉLATION POUR L'ADMINISTRATION DE RADIONUCLÉIDES
  申请人：HUTCHINSON FRED CANCER RES

  公开号：WO2018044812A3

  公开（公告）日：2018-06-07
• COMT INHIBITORS
  申请人：F.HOFFMANN-LA ROCHE AG

  公开号：EP1697394B1

  公开（公告）日：2007-03-21