2-<2-(methylsulfonyl)ethyl>naphthalene | 102072-41-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-<2-(methylsulfonyl)ethyl>naphthalene
• 英文别名: 2-(2-methanesulfonyloxyethyl)naphthalene；2-(naphthalen-2-yl)ethyl methanesulfonate；2-(2-mesyloxyethyl)naphthalene；methanesulfonic acid 2-naphthalen-2-yl-ethyl ester；2-Naphthaleneethanol, 2-methanesulfonate；2-naphthalen-2-ylethyl methanesulfonate
• CAS: 102072-41-3
• 化学式: C₁₃H₁₄O₃S
• 分子量: 250.318
• InChiKey: ZRGSOWABAKYBGO-UHFFFAOYSA-N

物化性质

• 沸点：
  456.4±24.0 °C(Predicted)
• 密度：
  1.249±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-<2-(methylsulfonyl)ethyl>naphthalene 在 N-甲基吗啉 、 盐酸 、 1-羟基苯并三唑 、 溶剂黄146 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 101.0h， 生成 [(S)-1-[(R)-1-({[Ethyl-(2-naphthalen-2-yl-ethyl)-carbamoyl]-methyl}-carbamoyl)-4-guanidino-butylcarbamoyl]-2-(4-hydroxy-phenyl)-ethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Peripherally acting enkephalin analogs. 2. Polar tri- and tetrapeptides

  摘要：

  The design, synthesis, and biological activity of a series of D-Arg2-enkephalin-derived tetrapeptide amides and tripeptide aralkylamides are reported. These polar analogues were designed to be excluded from the central nervous system with their action thus limited to peripheral opioid receptors. The effects of the nature of the aromatic ring, aryl ring substitution, and aralkylamine chain length on activity were investigated; in a number of cases the N-terminal amino group of Tyr1 was converted to a guanidino group to further increase hydrophilicity. The peptides were all synthesized by classical solution methodology. The opioid activity of the peptides was assessed in vitro on the guinea pig ileum and their antinociceptive activity was determined in vivo in chemically induced writhing models (peripheral activity) and in the hot-plate test (central activity), in rodents. That the analgesic effects were predominantly mediated in the periphery was demonstrated by antagonism of antinociception by the peripheral opioid antagonist N-methylnalorphine and by comparison of the activities in the writhing and hot-plate tests. As a class, the tetrapeptides were more potent than the tripeptides; N alpha-amidination generally increased activity. A number of compounds exhibited very potent opioid activity and had the desired pharmacological profile, indicating a high degree of peripheral selectivity.

  DOI：

  10.1021/jm00125a028
• 作为产物：
  描述：

  2-萘乙醇 、 甲基磺酰氯 在 4-甲基吡啶氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以98%的产率得到2-<2-(methylsulfonyl)ethyl>naphthalene
  参考文献：
  名称：

  通过 4-甲基吡啶 N-氧化物催化剂与 4Å 分子筛的组合进行无胺 O-磺酰化

  摘要：

  在室温下，在 4Å 分子筛存在下，使用 4-甲基吡啶N-氧化物开发了各种醇的无胺磺酰化。这种温和的方法以高收率得到各种磺酰化产物，可应用于碱敏感底物。

  DOI：

  10.1055/a-1865-2970

文献信息

• DERIVATIVES OF ALKYLPIPERAZINE AND ALKYLHOMOPIPERAZINE-CARBOXYLATES, PREPARATION METHOD THEREOF AND USE OF SAME AS FATTY ACID AMIDO HYDROLASE ENZYME INHIBITORS
  申请人：Abouabdellah Ahmed

  公开号：US20070027141A1

  公开（公告）日：2007-02-01

  The present invention comprises alkylpiperazine- and alkylhomopiperazine carboxylates and their derivatives, methods for their preparation and the therapeutic use thereof as fatty acid amido hydrolase (FAAH) enzyme inhibitors. These derivatives exert various pharmacological activities by interacting, inter alia, with cannabinoid and vanilloid receptors. By inhibiting the metabolic activity of the FAAH enzyme, compounds often responsible for the onset of disease and other pathological conditions are not generated and the incidence of the disease is greatly reduced.

  本发明涉及烷基哌嗪和烷基同源哌嗪羧酸盐及其衍生物，其制备方法以及作为脂肪酸酰胺水解酶（FAAH）酶抑制剂的治疗用途。这些衍生物通过与大麻素和辣椒素受体等相互作用，发挥各种药理活性。通过抑制FAAH酶的代谢活性，通常导致疾病发作和其他病理状况的化合物不会生成，疾病的发生率大大降低。
• Rapid Discovery of Highly Potent and Selective Inhibitors of Histone Deacetylase 8 Using Click Chemistry to Generate Candidate Libraries
  作者：Takayoshi Suzuki、Yosuke Ota、Masaki Ri、Masashige Bando、Aogu Gotoh、Yukihiro Itoh、Hiroki Tsumoto、Prima R. Tatum、Tamio Mizukami、Hidehiko Nakagawa、Shinsuke Iida、Ryuzo Ueda、Katsuhiko Shirahige、Naoki Miyata

  DOI：10.1021/jm300837y

  日期：2012.11.26

  μM), which was more potent than PCI-34058 (6) (IC50 = 0.31 μM), a known HDAC8 inhibitor. Molecular modeling suggested that the phenylthiomethyl group of C149 binds to a unique hydrophobic pocket of HDAC8, and the orientation of the phenylthiomethyl and hydroxamate moieties (fixed by the triazole moiety) is important for the potency and selectivity. The inhibitors caused selective acetylation of cohesin

  为了找到HDAC8选择性抑制剂，我们设计了一个HDAC抑制剂候选物库，每个候选物均包含一个与活性位点锌离子配位的锌结合基团，并通过三唑部分连接至一个与帽沿边缘上的残基相互作用的加帽结构活动站点。这些化合物通过点击化学合成。筛选鉴定出的HDAC8选择性抑制剂包括C149（IC 50 = 0.070μM），其比已知的HDAC8抑制剂PCI-34058（6）（IC 50 = 0.31μM）更有效。分子建模表明，C149的苯硫基甲基结合到HDAC8的独特疏水口袋，并且苯硫甲基和异羟肟酸酯部分（由三唑部分固定）的方向对于效价和选择性很重要。抑制剂引起细胞内黏附素的选择性乙酰化，并对T细胞淋巴瘤和神经母细胞瘤细胞产生生长抑制作用（GI 50 = 3–80μM）。这些发现表明，HDAC8-选择性抑制剂具有作为抗癌药的潜力。
• Structure-activity relationships of (arylalkyl)imidazole anticonvulsants: comparison of the (fluorenylalkyl)imidazoles with nafimidone and denzimol
  作者：David W. Robertson、Joseph H. Krushinski、E. E. Beedle、J. David Leander、David T. Wong、R. C. Rathbun

  DOI：10.1021/jm00159a004

  日期：1986.9

  fluorenyl, benzo[b]thienyl, and benzofuranyl aryl groups provided several highly active (arylalkyl)imidazole anticonvulsants. These structurally diverse aryl moieties, and comparable anticonvulsant activities, lend credence to the hypothesis that the pharmacophore of this class of anticonvulsants is the alkylimidazole portion of the molecule, with the lipophilic aryl portion enabling penetration of the

  （芳烷基）咪唑类是最近发现的并且在结构上不同的一类抗癫痫药。此类的两个独立发现的代表：地摩尔（α-[4-（2-苯基乙基）苯基] -1H-咪唑-1-乙醇）和萘啶酮（2-（1H-咪唑-1-基）-1-（2 -萘基萘酮）正在接受临床评估。我们的结构活性关系（SAR）研究表明，除了萘啶酮和苯并萘酚的萘基和苯乙基苯基芳基部分之外，芴基，苯并[b]噻吩基和苯并呋喃基芳基分别提供了几种高活性的（芳烷基）咪唑抗惊厥剂。这些结构上不同的芳基部分和可比较的抗惊厥活性使这一类抗惊厥药效基团是分子的烷基咪唑部分这一假设得到了证实，亲脂性芳基部分具有能够穿透血脑屏障的能力。我们将SAR研究的重点放在了（芴基烷基）咪唑系列上。该系列的代表性化合物是1-（9H-芴-2-基）-2-（1H-咪唑-1-基）乙酮。这种药物在抑制小鼠最大电击惊厥方面的功效是萘啶酮的两倍（分别为po ED50分别为25和56 mg / kg），而在
• [EN] TRYPTOPHAN HYDROXYLASE INHIBITORS AND METHODS OF THEIR USE<br/>[FR] INHIBITEURS DE LA TRYPTOPHANE HYDROXYLASE ET PROCÉDÉS D'UTILISATION ASSOCIÉS
  申请人：LEXICON PHARMACEUTICALS INC

  公开号：WO2010039957A1

  公开（公告）日：2010-04-08

  Compounds, compositions and methods of treating serotonin-mediated diseases and disorders are disclosed.

  揭示了治疗与血清素介导的疾病和紊乱的化合物、组合物和方法。
• Bis-Terminal Hydroxy Polyethers as All-Purpose, Multifunctional Organic Promoters: A Mechanistic Investigation and Applications
  作者：Ji Woong Lee、Hailong Yan、Hyeong Bin Jang、Hong Ki Kim、Sung-Woo Park、Sungyul Lee、Dae Yoon Chi、Choong Eui Song

  DOI：10.1002/anie.200903903

  日期：2009.9.28

  Achiral polyether derivatives have been shown to dramatically accelerate SN2 reactions by the simultaneous activation of both the nucleophile (KF) and electrophile (sulfonate; see picture). By using chiral variants as catalysts, the desilylative kinetic resolution of the silyl ethers of racemic secondary alcohols has been achieved. Density functional calculations provide detailed insight into the modes

  已显示非手性聚醚衍生物可通过亲核试剂（KF）和亲电试剂（磺酸盐；见图）的同时活化来显着加速S N 2反应。通过使用手性变体作为催化剂，已获得外消旋仲醇的甲硅烷基醚的脱甲硅烷基的动力学拆分。密度泛函计算可深入了解此类有机促进剂的作用方式。