6-苯基硫烷基己酸 | 325698-86-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 6-苯基硫烷基己酸
• 英文名称: 6-(phenylthio)hexanoic acid
• 英文别名: 6-Phenylsulfanylhexanoic acid
• CAS: 325698-86-0
• 化学式: C₁₂H₁₆O₂S
• 分子量: 224.324
• InChiKey: LPAASVMIRJIDQI-UHFFFAOYSA-N

物化性质

• 沸点：
  380.7±25.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-苯基硫烷基己酸 在 草酰氯 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 6-(phenylsulfinyl)-1-(5-(pyridin-2-yl)oxazol-2-yl)hexan-1-one
  参考文献：
  名称：

  Structure−Activity Relationships of α-Ketooxazole Inhibitors of Fatty Acid Amide Hydrolase

  摘要：

  A systematic study of the structure-activity relationships of 2b (OL-135), a potent inhibitor of fatty acid amide hydrolase (FAAH), is detailed targeting the C2 acyl side chain. A series of aryl replacements or substituents for the terminal phenyl group provided effective inhibitors (e.g., 5c, aryl = 1- napthyl, K-i = 2.6 nM), with 5hh (aryl = 3-ClPh, K-i = 900 pM) being 5-fold more potent than 2b. Conformationally restricted C2 side chains were examined, and many provided exceptionally potent inhibitors, of which 11j (ethylbiphenyl side chain) was established to be a 750 pM inhibitor. A systematic series of heteroatoms (O, NMe, S), electron-withdrawing groups (SO, SO2), and amides positioned within and hydroxyl substitutions on the linking side chain were investigated, which typically led to a loss in potency. The most tolerant positions provided effective inhibitors (12p, 6-position S, K-i = 3 nM, or 13d, 2-position OH, K-i = 8 nM) comparable in potency to 2b. Proteome-wide screening of selected inhibitors from the systematic series of > 100 candidates prepared revealed that they are selective for FAAH over all other mammalian serine proteases.

  DOI：

  10.1021/jm061414r
• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以18%的产率得到6-苯基硫烷基己酸
  参考文献：
  名称：

  吉非罗齐衍生物作为可溶性鸟苷酸环化酶的激活剂——结构-活性研究

  摘要：

  先前的研究表明，抗高血脂药物吉非贝齐可作为 NO 受体可溶性鸟苷酸环化酶的 NO 和血红素非依赖性激活剂。合成了一系列新的吉非罗齐衍生物并评估了 sGC 的活化作用。构效关系研究确定了吉非罗齐支架中不利于 sGC 激活的位置以及可修正以优化修饰的位置。与吉非贝齐相比，化合物7c和15b是纯化 sGC 的 cGMP 形成活性的更有效激活剂，并且表现出预收缩的小鼠胸主动脉环的增强松弛。这些研究建立了进一步改进基于吉非贝齐支架的 sGC 激活剂所需的总体框架。

  DOI：

  10.1016/j.ejmech.2021.113729

文献信息

• Synthesis of a Wide Range of Thioethers by Indium Triiodide Catalyzed Direct Coupling between Alkyl Acetates and Thiosilanes
  作者：Yoshihiro Nishimoto、Aya Okita、Makoto Yasuda、Akio Baba

  DOI：10.1021/ol300450j

  日期：2012.4.6

  An indium triiodide-catalyzed substitution of the acetoxy group in alkyl acetates with thiosilanes provides access to a variety of thioethers. The method is efficient for a wide scope of acetates such as primary alkyl, secondary alkyl, tertiary alkyl, allylic, benzylic, and propargylic acetates.

  三碘化铟催化的乙酸烷基酯中的乙酰氧基被硫代硅烷取代，从而可以使用多种硫醚。该方法对于各种乙酸酯如伯烷基，仲烷基，叔烷基，烯丙基，苄基和炔丙基乙酸是有效的。
• Synthesis, Characterization and Anti-Cancer Activity of Hydrazide Derivatives Incorporating a Quinoline Moiety
  作者：Murat Bingul、Owen Tan、Christopher Gardner、Selina Sutton、Greg Arndt、Glenn Marshall、Belamy Cheung、Naresh Kumar、David Black

  DOI：10.3390/molecules21070916

  日期：——

  lin-3-yl)methylene)-3-(phenylthio)propanehydrazide scaffold 18 has led to the development of a new series of biologically active hydrazide compounds. The parent compound 18 and new quinoline derivatives 19–26 were prepared from the corresponding quinoline hydrazones and substituted carboxylic acids using EDC-mediated peptide coupling reactions. Further modification of the parent compound 18 was achieved

  新型（E）-N'-（（2-氯-7-甲氧基喹啉-3-基）亚甲基）-3-（苯硫基）丙酰肼支架18的鉴定导致了一系列新的生物活性酰肼化合物的开发. 使用 EDC 介导的肽偶联反应，从相应的喹啉腙和取代的羧酸制备母体化合物 18 和新的喹啉衍生物 19-26。母体化合物 18 的进一步修饰是通过用其他芳族系统替换喹啉部分来实现的。评估了所有新合成的化合物对 SH-SY5Y 和 Kelly 神经母细胞瘤细胞系以及 MDA-MB-231 和 MCF-7 乳腺癌细胞系的抗癌活性。类似物 19 和 22 显着降低神经母细胞瘤癌细胞的细胞活力，具有微摩尔效力和对正常细胞的显着选择性。喹啉酰肼 22 还诱导 G1 细胞周期停滞，以及 p27kip1 细胞周期调节蛋白的上调。
• TRICYCLIC INHIBITORS OF FATTY ACID AMIDE HYDROLASE
  申请人：Boger Dale L.

  公开号：US20100216750A1

  公开（公告）日：2010-08-26

  A series of substituted oxazole compounds having an alpha keto side chain at the 2 position and an aromatic, heteroaromatic or heterocycle substituent at the 5 position are disclosed. These compounds exhibit inhibition of fatty acid amid hydrolase and arc useful for treatment of malconditions involving that enzyme.

  本发明揭示了一系列取代的噁唑化合物，其中在2位具有α-酮基侧链，在5位具有芳香、杂芳或杂环取代基。这些化合物表现出脂肪酸酰胺水解酶的抑制作用，并且对于治疗涉及该酶的恶性状况是有用的。
• New polyhydroxyalkanoate copolymer, resin composition, molded product, toner, image forming method and image forming apparatus
  申请人：Yano Tetsuya

  公开号：US20060040196A1

  公开（公告）日：2006-02-23

  A polyhydroxyalkanoate copolymer comprises one kind of unit of —[OCH((CH 2 ) x —SOC 6 H 5 R)CH 2 CO]— (n= 1 - 7 )   ( 1 ) (wherein R is any one of H, halogen, CN, NO 2 , COOR′, SO 2 R″ (R′ is any one of H, Na, K, CH 3 and C 2 H 5 ; R″ is any one of OH, ONa, OK, halogen, OCH 3 and OC 2 H 5 ), CH 3 , C 2 H 5 , C 3 H 7 , (CH 3 ) 2 —CH and (CH 3 ) 3 —C) and —[OCH((CH 2 ) x —SO 2 C 6 H 5 R)CH 2 CO]— (n= 1 - 7 )   ( 2 ) (wherein R is any one of H, halogen, CN, NO 2 , COO R′, SO 2 R″ (R′ is any one of H, Na, K, CH 3 and C 2 H 5 ; R″ is any one of OH, ONa, OK, halogen, OCH 3 and OC 2 H 5 ), CH 3 , C 2 H 5 , C 3 H 7 , (CH 3 ) 2 —CH and (CH 3 ) 3 —C) and at least one unit of chemical formulae ( 3 ) to ( 6 ): —[OCH((CH 2 ) m —Rz)CH 2 CO]— (n= 1 - 8 )   ( 3 ) (wherein Rz comprises a residue having either a phenyl structure or a thienyl structure), —[OCH((CH 2 ) k —C 6 H 11 Ra)CH 2 CO]— (n= 1 - 8 )   ( 4 ) (wherein R a is any one of H, CN, NO 2 , halogen, CH 3 , C 2 H 5 , C 3 H 7 , CF 3 , C 2 F 5 and C 3 F 7 ) —[OCH((CH 2 ) n —CH═CH 2 )CH 2 CO]— (n= 1 - 8 )   ( 5 ), and —[OCH((CH 2 ) n —COORb)CH 2 CO]— (n= 1 - 8 )   ( 6 ) (wherein R b is any one of H, Na and K).

  聚羟基烷酸酯共聚物由以下一种单元组成 -[OCH((CH 2 ) x -SOC 6 H 5 R)CH 2 CO]- (n= 1 - 7 ) ( 1 ) (其中 R 是 H、卤素、CN、NO 2 、COOR′、SO 2 R″（R′是 H、Na、K、CH 3 和 C 2 H 5 R″是 OH、ONa、OK、卤素、OCH 3 和 OC 2 H 5 ）、CH 3 , C 2 H 5 , C 3 H 7 , (CH 3 ) 2 -CH和(CH 3 ) 3 -C）和 -[OCH((CH 2 ) x -SO 2 C 6 H 5 R)CH 2 CO]- (n= 1 - 7 ) ( 2 ) (其中 R 是 H、卤素、CN、NO 2 、COO R′、SO 2 R″（R′是 H、Na、K、CH 3 和 C 2 H 5 R″是 OH、ONa、OK、卤素、OCH 3 和 OC 2 H 5 ）、CH 3 , C 2 H 5 , C 3 H 7 , (CH 3 ) 2 -CH和(CH 3 ) 3 -C）和至少一个化学式单位 ( 3 )至( 6 ): -[OCH((CH 2 ) m -Rz)CH 2 CO]- (n= 1 - 8 ) ( 3 ) (其中 Rz 包括具有苯基结构或噻吩基结构的残基）、 -[OCH((CH 2 ) k -C 6 H 11 Ra)CH 2 CO]- (n= 1 - 8 ) ( 4 ) (其中 R a 是 H、CN、NO 2 卤素、CH 3 , C 2 H 5 , C 3 H 7 , CF 3 , C 2 F 5 和 C 3 F 7 ) -[OCH((CH 2 ) n -CH═CH 2 ) CH 2 CO]- (n= 1 - 8 ) ( 5 和 -[OCH((CH 2 ) n -COORb)CH 2 CO]- (n= 1 - 8 ) ( 6 ) (其中 R b 是 H、Na 和 K 中的任意一种）。
• Direct synthesis of carboxylic acids from organoboranes
  作者：Shoji Hara、Kotaro Kishimura、Akira Suzuki、Ranjit S. Dhillon

  DOI：10.1021/jo00313a023

  日期：1990.12

  Direct synthesis of carboxylic acids through a two carbon atom homologation from organoboranes has been achieved, by the reaction with the dianion of phenoxyacetic acid. It is now possible to synthesize alkanoic, alkenoic, or alkynoic acids, from the corresponding alkenes, dienes, or enynes, respectively, via hydroboration. The reaction is tolerant of various functional groups present in alkenes, thus giving the corresponding carboxylic acids with chloro, sulfide, ether, acetal, and thioacetal functionalities in good yields.