1-(3-pentyloxyphenyl)ethanone | 37062-69-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-pentyloxyphenyl)ethanone
• 英文别名: 1-(3-(Pentyloxy)phenyl)ethanone；1-(3-pentoxyphenyl)ethanone
• CAS: 37062-69-4
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: MHKKOAAKTHSSOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-pentyloxyphenyl)ethanone 在 盐酸羟胺 、 sodium ethanolate 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 52.75h， 生成 N-(1-adamantyl)-5-(3-pentyloxyphenyl)isoxazole-3-carboxamide
  参考文献：
  名称：

  3-Carboxamido-5-aryl-isoxazoles as new CB2 agonists for the treatment of colitis

  摘要：

  Recent investigations showed that anandamide, the main endogenous ligand of CB1 and CB2 cannabinoid receptors, possesses analgesic, antidepressant and anti-inflammatory effects. In the perspective to treat inflammatory bowel disease (IBD), our approach was to develop new selective CB2 receptor agonists without psychotropic side effects associated to CB1 receptors. In this purpose, a new series of 3-carboxamido-5-aryl-isoxazoles, never described previously as CB2 receptor agonists, was designed, synthesized and evaluated for their biological activity. The pharmacological results have identified great selective CB2 agonists with in vivo anti-inflammatory activity in a DSS-induced acute colitis mouse model. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.010
• 作为产物：
  描述：

  1-溴戊烷 、 3-羟基苯乙酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以90%的产率得到1-(3-pentyloxyphenyl)ethanone
  参考文献：
  名称：

  3-Carboxamido-5-aryl-isoxazoles as new CB2 agonists for the treatment of colitis

  摘要：

  Recent investigations showed that anandamide, the main endogenous ligand of CB1 and CB2 cannabinoid receptors, possesses analgesic, antidepressant and anti-inflammatory effects. In the perspective to treat inflammatory bowel disease (IBD), our approach was to develop new selective CB2 receptor agonists without psychotropic side effects associated to CB1 receptors. In this purpose, a new series of 3-carboxamido-5-aryl-isoxazoles, never described previously as CB2 receptor agonists, was designed, synthesized and evaluated for their biological activity. The pharmacological results have identified great selective CB2 agonists with in vivo anti-inflammatory activity in a DSS-induced acute colitis mouse model. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.010

文献信息

• Design, Synthesis, Biological Evaluation and Inhibition Mechanism of 3-/4-Alkoxy Phenylethylidenethiosemicarbazides as New, Potent and Safe Tyrosinase Inhibitors
  作者：Senchuan Song、Yuliang Mai、Huahong Shi、Bing Liao、Fei Wang

  DOI：10.1248/cpb.c19-00949

  日期：2020.4.1

  Tyrosinase plays important roles in many different disease related processes, and the development of its inhibitors is particularly important in biotechnology. In this study, thirty-nine 3-/4-alkoxyphenylethylidenethiosemicarbazides were synthesized as novel tyrosinase inhibitors based on structure-based molecular design. Our experimental results demonstrated that thirty-one of them possess remarkable tyrosinase inhibitory activities with IC50 value below 1 µM, and 5a, 6e, 6g and 6t did not display any toxicity to 293T cell line at the concentration of 1000 µmol/L. According to the inhibitory activities, several compounds were selected for detail investigation on the structure–activity relationships (SARs), mechanisms of enzyme inhibition, inhibitory kinetics and cytotoxicity. In particular, the interaction between the selected inhibitors and the active center of tyrosinase was considered and discussed in detail based on their structural characteristics. Taken together, the results presented here demonstrated that the newly designed compounds are promising candidates for the treatment of tyrosinase-related disorders and further development of them may have significant contribution in biomedical science.

  酪氨酸酶在多种与疾病相关的过程中扮演重要角色，其抑制剂的研发在生物技术领域尤为重要。本研究基于结构导向的分子设计，合成了39种新颖的3-/4-烷氧基苯乙烯基二唑半卡巴唑类化合物作为酪氨酸酶抑制剂。我们的实验结果显示，其中31种化合物的酪氨酸酶抑制活性显著，IC50值低于1µM，且5a、6e、6g和6t在1000µmol/L浓度下对293T细胞系无毒性。根据抑制活性，选取了若干化合物详细研究了构效关系、酶抑制机制、抑制动力学及细胞毒性。特别是，基于这些化合物的结构特征，详细考虑并讨论了所选抑制剂与酪氨酸酶活性中心的相互作用。综上所述，本研究结果表明，新设计的化合物是治疗与酪氨酸酶相关疾病的潜在候选药物，其进一步开发可能对生物医学科学产生重大贡献。
• SKIN WHITENING AGENT CONTAINING NOVEL CYCLIC COMPOUND
  申请人：RNS CO.,LTD.

  公开号：US20160221921A1

  公开（公告）日：2016-08-04

  Provided is a derivative or a polyhydroxy cyclic compound represented by Formula I or a pharmacologically acceptable salt thereof with excellent whitening effects, comprising; wherein circle around (A)} is derived from an aromatic cyclic compound, B is hydrogen, oxo (═O), amino (—NH 2 ), imino (═NH), or a saturated or unsaturated straight or branched alkyl, alkoxy, monoalkylamino, or dialkylamino group having 1 to 10 carbon atoms, C n , C n+1 and C n+2 are three neighboring carbon atoms present in the aromatic cyclic compound, wherein n is a positive integer, R 1 is hydrogen, hydroxy, or a saturated or unsaturated straight or branched alkyl or alkoxy group, X and Y are selected from a group consisting of hydrogen, hydroxy, and a saturated or unsaturated straight or branched alkoxy, or acyloxy group, and one of X and Y is hydrogen, R 2 , R 3 , R 4 and R 5 are each independently at least one substituent selected from a group consisting of hydrogen, alkyl, alkoxy, acyloxy, acyloxymethyl, oxo, hydroxy, vinyl, nitrile, carboxaldehyde, carbonitrile and aldehyde.

  提供的是一种由化学式I表示的衍生物或多羟基环化合物，或其药理学上可接受的盐，具有出色的美白效果，包括；其中圆圈A}源自芳香环化合物，B为氢、氧化物(═O)、氨基(—NH2)、亚胺基(═NH)或具有1至10个碳原子的饱和或不饱和直链或支链烷基、烷氧基、单烷基氨基或二烷基氨基基团，Cn、Cn+1和Cn+2是芳香环化合物中存在的三个相邻碳原子，其中n为正整数，R1为氢、羟基或饱和或不饱和直链或支链烷基或烷氧基，X和Y从氢、羟基和饱和或不饱和直链或支链烷氧基或酰氧基组成的一组中选择，并且X和Y中的一个为氢，R2、R3、R4和R5分别独立地至少为来自氢、烷基、烷氧基、酰氧基、酰氧甲基、氧化物、羟基、乙烯基、腈基、羧醛基、碳腈基和醛基的取代基组成的一组中的至少一种取代基。
• TETRAZOLINONE COMPOUND AND APPLICATIONS THEREOF
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：US20150299146A1

  公开（公告）日：2015-10-22

  The compound represented by formula (1): wherein R 4 and R 5 each represents a hydrogen atom, a halogen atom, or a C1-C3 alkyl group; R 6 represents a C1-C4 alkyl group, a C3-C6 cycloalkyl group, or the like; R 7 , R 8 , and R 9 each represents a hydrogen atom, a halogen atom, or the like; R 10 represents a C1-C3 alkyl group, or the like; R 13 represents a C1-C3 alkyl group, or the like; and Q represents a phenyl group, or the like; has an excellent control effect on pests.

  式(1)所代表的化合物：其中，R4和R5分别表示氢原子、卤素原子或C1-C3烷基；R6表示C1-C4烷基、C3-C6环烷基或类似物；R7、R8和R9分别表示氢原子、卤素原子或类似物；R10表示C1-C3烷基或类似物；R13表示C1-C3烷基或类似物；Q表示苯基或类似物。该化合物对害虫有极好的控制效果。
• TETRAZOLINONE COMPOUND AND USE THEREOF
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP2927218B1

  公开（公告）日：2018-07-04
• Sadashiva, Bukkinakere K.; Prasad, Veena, Journal of the Chemical Society. Perkin transactions II, 1996, # 4, p. 755 - 760
  作者：Sadashiva, Bukkinakere K.、Prasad, Veena

  DOI：——

  日期：——