6-(trityloxy)hexanoic acid | 220129-97-5

• 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: 6-(trityloxy)hexanoic acid
• 英文别名: 6-trityloxyhexanoic acid；trityl-O-(CH2)5COOH
• CAS: 220129-97-5
• 化学式: C₂₅H₂₆O₃
• 分子量: 374.48
• InChiKey: JOGZKQYSXVDIQC-UHFFFAOYSA-N

物化性质

• 熔点：
  117-119 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  519.1±38.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  6-(trityloxy)hexanoic acid 在 吗啉 、 甲醇 、 四(三苯基膦)钯 、 对甲苯磺酸 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 13.0h， 生成
  参考文献：
  名称：

  New Antibacterial Agents Derived from the DNA Gyrase Inhibitor Cyclothialidine

  摘要：

  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.

  DOI：

  10.1021/jm0310232
• 作为产物：
  描述：

  6-trityloxyhexanal 在 potassium permanganate 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 6-(trityloxy)hexanoic acid
  参考文献：
  名称：

  New Antibacterial Agents Derived from the DNA Gyrase Inhibitor Cyclothialidine

  摘要：

  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.

  DOI：

  10.1021/jm0310232
• 作为试剂：
  描述：

  、 methyl 6-trityloxyhexanoate 、 methyl 9-trityloxynonanoate 、 methyl 12-trityloxydodecanoate 在 6-(trityloxy)hexanoic acid 、 9-trityloxynonanoic acid 作用下， 以12-trityloxydodecanoic acid 16c were isolated的产率得到12-triphenylmethyloxydodecanoic acid
  参考文献：
  名称：

  NOVEL GHRELIN ANALOGUES

  摘要：

  本发明提供了具有高亲和力的 ghrelin 类似物，用于疾病细胞中的靶受体，以及利用这些类似物进行诊断和治疗的方法。

  公开号：

  US20110110855A1

文献信息

• [EN] NUCLEOTIDE DERIVATIVES AND METHODS OF USE THEREOF<br/>[FR] DÉRIVÉS NUCLÉOTIDIQUES ET LEURS MÉTHODES D'UTILISATION
  申请人：UNIV COLUMBIA

  公开号：WO2017205336A1

  公开（公告）日：2017-11-30

  Disclosed herein, inter alia, are compounds, compositions, and methods of thereof in the sequencing a nucleic acid.

  本公开的内容包括化合物、组合物以及在核酸测序中的方法。
• Fluorine and Rhenium Substituted Ghrelin Analogues as Potential Imaging Probes for the Growth Hormone Secretagogue Receptor
  作者：Dina Rosita、Matthew A. DeWit、Leonard G. Luyt

  DOI：10.1021/jm8014519

  日期：2009.4.23

  prepared containing rhenium, as a surrogate metal for technetium-99m, with a cyclopentadienylrhenium tricarbonyl being situated at the terminus of the residue-3 side chain, yielding compounds the best of which had a 35 nM IC50. This represents a rare case of incorporating rhenium into a peptide structure where the metal complex is required for biological activity. These fluorine and rhenium derivatives demonstrate

  在努力创建针对生长激素促分泌素受体（GHSR）的成像探针的过程中，我们现在报告了通过修饰正辛酰基Ser-3侧链设计和合成含氟和rh的生长素释放肽类似物的过程。使用二氨基丙酸（Dpr）作为残基-3，设计了氟类似物，使氟原子位于脂族链的末端。制备了截短的ghrelin（1-5）和ghrelin（1-14）含氟类似物，其中最好的类似物具有用于GHSR的28 nM IC 50。还制备了Ghrelin（1-14）类似物，其中含有rh，作为m 99m的替代金属，三羰基环戊二烯基r位于残基3侧链的末端，产生的化合物中最好的是35 nM IC50。这代表了将rh掺入肽结构的罕见情况，其中金属配合物是生物活性所必需的。这些氟和rh衍生物表现出修饰ghrelin的Ser-3侧链的能力，以便为GHSR创建成像探针。
• Synthesis of analogs of 1,1-linked galactosyl mannoside as mimetics of sialyl Lewis X tetrasaccharide
  作者：Kazumi Hiruma、Osamu Kanie、Chi-Huey Wong

  DOI：10.1016/s0040-4020(98)00990-9

  日期：1998.12

  for the incorporation of hydrophobic groups with and without positive or negative charge to position-6 of the mannose residue in the 1,1-linked disaccharide as mimetics of sialyl Lewis X tetrasaccharide in order to enhance binding affinity to selectins.

  已经开发了将带有或不带正电荷或不带正电荷或不带正电荷的疏水基团掺入到1，1-连接的二糖中的甘露糖残基的6位上的方法，以作为唾液酸路易斯X四糖的模拟物，以增强与选择素的结合亲和力。
• Synthesis, DNA-Binding and Antiproliferative Properties of Acridine and 5-Methylacridine Derivatives
  作者：Rubén Ferreira、Anna Aviñó、Stefania Mazzini、Ramon Eritja

  DOI：10.3390/molecules17067067

  日期：——

  Several acridine derivatives were synthesized and their anti-proliferative activity was determined. The most active molecules were derivatives of 5-methylacridine-4-carboxylic acid. The DNA binding properties of the synthesized acridines were analyzed by competitive dialysis and compared with the anti-proliferative activities. While inactive acridine derivatives showed high selectivity for G-quadruplex structures, the most active 5-methylacridine-4-carboxamide derivatives had high affinity for DNA but showed poor specificity. An NMR titration study was performed with the most active 5-methylacridine-4-carboxamide, confirming the high affinity of this compound for both duplex and quadruplex DNAs.

  我们合成了几种吖啶衍生物，并测定了它们的抗增殖活性。活性最强的分子是 5-甲基吖啶-4-羧酸的衍生物。通过竞争性透析分析了合成的吖啶类化合物的 DNA 结合特性，并将其与抗增殖活性进行了比较。非活性吖啶衍生物对 G-四链结构具有高选择性，而活性最高的 5-甲基吖啶-4-甲酰胺衍生物对 DNA 具有高亲和力，但特异性较差。对活性最强的 5-甲基吖啶-4-甲酰胺进行了核磁共振滴定研究，证实该化合物对双链和四链 DNA 都有很高的亲和力。
• Ghrelin analogues
  申请人：Luyt Leonard G.

  公开号：US08623326B2

  公开（公告）日：2014-01-07

  Ghrelin analogues having high affinity for a target receptor in diseased cells are provided, as well as methods of diagnosis and treatment utilizing such analogues.

  提供了对疾病细胞中靶受体具有高亲和力的胃饥饿素类似物，以及利用这些类似物进行诊断和治疗的方法。