7-(trityloxy)heptanoic acid | 173152-99-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 7-(trityloxy)heptanoic acid
• 英文别名: 7-trityloxyheptanoic acid；7-trityloxy-heptanoic acid
• CAS: 173152-99-3
• 化学式: C₂₆H₂₈O₃
• 分子量: 388.507
• InChiKey: NUORLXYNQUZBNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-(trityloxy)heptanoic acid 在 三氟甲磺酸酐 、 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 oxocan-2-one
  参考文献：
  名称：

  醇和醚在室温下直接酰胺化成酰胺：合成的“酰胺策略”

  摘要：

  最后一分钟的交易：据报道，醚和醇在酰胺的直接内酯化反应在室温下，在温和条件下进行（见方案）。这允许在合成序列中有效节省多达两个非生产性的顺序脱保护操作。描述了机理研究，并概述了利用该官能团的双重鲁棒性/后期选择性激活特性的新“酰胺策略”。

  DOI：

  10.1002/chem.201203906
• 作为产物：
  描述：

  1,7-庚二醇 在 吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 sodium chlorite 作用下， 以 aq. phosphate buffer 、 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 7-(trityloxy)heptanoic acid
  参考文献：
  名称：

  醇和醚在室温下直接酰胺化成酰胺：合成的“酰胺策略”

  摘要：

  最后一分钟的交易：据报道，醚和醇在酰胺的直接内酯化反应在室温下，在温和条件下进行（见方案）。这允许在合成序列中有效节省多达两个非生产性的顺序脱保护操作。描述了机理研究，并概述了利用该官能团的双重鲁棒性/后期选择性激活特性的新“酰胺策略”。

  DOI：

  10.1002/chem.201203906

文献信息

• Mono or bicyclic DNA gyrase inhibitors
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0675122A2

  公开（公告）日：1995-10-04

  The present invention relates to mono- or bicyclic compounds of the general formula wherein X1is -S- or -SO-; R1is hydrogen, halogen or lower alkyl, optionally substituted by halogen ; R2is hydrogen, hydroxy, amino, lower alkylamino, di-lower alkylamino, optionally substituted lower alkoxy or a group -OP; OPis an easily hydrolyzable group; R3is hydrogen, hydroxy, lower alkyl, halogen or a group -OP; R4is halogen, hydroxy or a group -OP; R5is hydrogen, cyano, optionally substituted esterified carboxy or optionally substituted amidated (thio)carboxy, optionally substituted alkyl, optionally substituted alkenyl or optionally substituted heterocyclyl; R6is -NR7-A, -N=B or optionally substituted heterocyclyl, in which R7 is hydrogen or lower alkyl, A is optionally substituted iminoyl, optionally substituted (thio)acyl, optionally substituted esterified carboxy, optionally substituted amidated (thio)carboxy or optionally substituted heterocyclyl and B is optionally substituted alkylidene; R0is cyano, optionally substituted esterified carboxy or optionally substituted heterocyclyl, or wherein R0 and R6taken together represent a group         -CO-O-Q-X2-N(R7)-, wherein R7is as above, and X2is (thio)carbonyl or heterocyclyl; Qis -CH(R8)- or -CH(R8)-W-; R8is hydrogen or optionally substituted lower alkyl, and Wis optionally substituted mono-, di-, tri-, tetra- or pentamethylene, provided that when W is monomethylene X2 is other than (thio)carbonyl, and pharmaceutically acceptable salts of the mono- or bicyclic compounds of formula I carrying an acidic and/or basic substituent. These compounds of formula I as well as their pharmaceutically acceptable salts inhibit DNA gyrase activity in bacteria and possess antibiotic, especially antibacterial activity against microorganisms and can be used in the control or prevention of infectious diseases.

  本发明涉及通式如下的单环或双环化合物 其中 X1是-S-或-SO-； R1是氢、卤素或低级烷基，任选被卤素取代； R2 是氢、羟基、氨基、低级烷基氨基、二低级烷基氨基、任选被取代的低级烷氧基或基团 -OP； OP 是易水解基团； R3 是氢、羟基、低级烷基、卤素或基团 -OP R4 是卤素、羟基或基团 -OP R5是氢、氰基、任选取代的酯化羧基或任选取代的酰胺化（硫代）羧基、任选取代的烷基、任选取代的烯基或任选取代的杂环基； R6是-NR7-A、-N=B或任选取代的杂环基，其中R7是氢或低级烷基，A是任选取代的亚氨基酰基、任选取代的（硫代）酰基、任选取代的酯化羧基、任选取代的酰胺化（硫代）羧基或任选取代的杂环基，B是任选取代的亚烷基； R0 是氰基、任选取代的酯化羧基或任选取代的杂环基，或其中 R0 和 R6 合在一起代表一个基团 -CO-O-Q-X2-N(R7)-、 其中 R7 如上，以及 X2 是（硫代）羰基或杂环基； Q是-CH(R8)-或-CH(R8)-W-； R8 是氢或任选取代的低级烷基，以及 Wis 任选取代的一亚甲基、二亚甲基、三亚甲基、四亚甲基或五亚甲基，但当 W 为一亚甲基时，X2 不是（硫代）羰基、 和 带有酸性和/或碱性取代基的式 I 单环或双环化合物的药学上可接受的盐。 这些式 I 化合物及其药学上可接受的盐类可抑制细菌中 DNA 回旋酶的活性，并具有抗生素活性，特别是对微生物的抗菌活性，可用于控制或预防传染性疾病。
• New Antibacterial Agents Derived from the DNA Gyrase Inhibitor Cyclothialidine
  作者：Peter Angehrn、Stefan Buchmann、Christoph Funk、Erwin Goetschi、Hans Gmuender、Paul Hebeisen、Dirk Kostrewa、Helmut Link、Thomas Luebbers、Raffaello Masciadri、Joergen Nielsen、Peter Reindl、Fabienne Ricklin、Anne Schmitt-Hoffmann、Frank-Peter Theil

  DOI：10.1021/jm0310232

  日期：2004.3.1

  Cyclothialidine (1, Ro 09-1437) is a potent DNA gyrase inhibitor that was isolated from Streptomyces filipinensis NR0484 and is a member of a new family of natural products. It acts by competitively inhibiting the ATPase activity exerted by the B subunit of DNA gyrase but barely exhibits any growth inhibitory activity against intact bacterial cells, presumably due to insufficient permeation of the cytoplasmic membrane. To explore the antibacterial potential of 1, we developed a flexible synthetic route allowing for the systematic modification of its structure. From a first set of analogues, structure-activity relationships (SAR) were established for different substitution patterns, and the 14-hydroxylated, bicyclic core (X) of 1 seemed to be the structural prerequisite for DNA gyrase inhibitory activity. The variation of the lactone ring size, however, revealed that activity can be found among 11- to 16-membered lactones, and even seco-analogues were shown to maintain some enzyme inhibitory properties, thereby reducing the minimal structural requirements to a rather simple, hydroxylated benzyl sulfide (XI). On the basis of these "minimal structures" a modification program afforded a number of inhibitors that showed in vitro activity against Gram-positive bacteria. The best activities were displayed by 14-membered lactones, and representatives of this subclass exhibit excellent and broad in vitro antibacterial activity against Gram-positive pathogens, including Staphylococcus aureus, Streptococcus pyogenes, and Enterococcus faecalis, and overcome resistance against clinically used drugs. By improving the pharmacokinetic properties of the most active compounds (94, 97), in particular by lowering their lipophilic properties, we were able to identify congeners of cyclothialidine (1) that showed efficacy in vivo.
• US5589473A
  申请人：——

  公开号：US5589473A

  公开（公告）日：1996-12-31
• US5594135A
  申请人：——

  公开号：US5594135A

  公开（公告）日：1997-01-14
• US5665746A
  申请人：——

  公开号：US5665746A

  公开（公告）日：1997-09-09