1-BOC-4-(2-((甲基磺酰基)氧基)丁基)哌啶 | 199538-93-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 1-BOC-4-(2-((甲基磺酰基)氧基)丁基)哌啶
• 英文名称: tert-butyl 4-{4-[(methylsulfonyl)oxy]butyl}piperidine-1-carboxylate
• 英文别名: 1-Boc-4-(2-((methylsulfonyl)oxy)butyl)piperidine；4-(4-methanesulfonyloxy-butyl)-piperidine-1-carboxylic acid tert-butyl ester；tert-butyl 4-(4-methylsulfonyloxybutyl)piperidine-1-carboxylate
• CAS: 199538-93-7
• 化学式: C₁₅H₂₉NO₅S
• 分子量: 335.465
• InChiKey: GXTLTGWJLSTSME-UHFFFAOYSA-N

物化性质

• 沸点：
  455.6±18.0 °C(Predicted)
• 密度：
  1.121±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-BOC-4-(2-((甲基磺酰基)氧基)丁基)哌啶 在 盐酸 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 3.0h， 生成 1-[4-(piperidin-4-yl)butyl]indole
  参考文献：
  名称：

  （吲哚基烷基）哌啶氨基甲酸酯作为脂肪酸酰胺水解酶（FAAH）的抑制剂† ‡

  摘要：

  合成了一系列苯基4-[（吲哚-1-基）烷基]哌啶氨基甲酸酯，并测试了其对内源性大麻素降解酶脂肪酸酰胺水解酶（FAAH）的抑制作用以及在大鼠肝脏S9馏分和猪血浆中的代谢稳定性。结构-活性关系研究表明，连接吲哚和哌啶杂环的烷基间隔基的长度变化，在吲哚环中引入取代基，哌嗪骨架取代哌啶以及哌啶环系统的开放均会影响活性显着地。该化合物类别的代谢稳定性被证明明显高于相应的苯基N-（吲哚-1-基烷基）氨基甲酸酯。

  DOI：

  10.1039/c6md00683c
• 作为产物：
  描述：

  甲基磺酰氯 、 4-(4-羟基丁基)哌啶-1-甲酸叔丁酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以99%的产率得到1-BOC-4-(2-((甲基磺酰基)氧基)丁基)哌啶
  参考文献：
  名称：

  （吲哚基烷基）哌啶氨基甲酸酯作为脂肪酸酰胺水解酶（FAAH）的抑制剂† ‡

  摘要：

  合成了一系列苯基4-[（吲哚-1-基）烷基]哌啶氨基甲酸酯，并测试了其对内源性大麻素降解酶脂肪酸酰胺水解酶（FAAH）的抑制作用以及在大鼠肝脏S9馏分和猪血浆中的代谢稳定性。结构-活性关系研究表明，连接吲哚和哌啶杂环的烷基间隔基的长度变化，在吲哚环中引入取代基，哌嗪骨架取代哌啶以及哌啶环系统的开放均会影响活性显着地。该化合物类别的代谢稳定性被证明明显高于相应的苯基N-（吲哚-1-基烷基）氨基甲酸酯。

  DOI：

  10.1039/c6md00683c

文献信息

• Bicyclic heteroaryl-substituted imidazoles as modulators of the histamine H4 receptor
  申请人：Kindrachuk David E.

  公开号：US20090156613A1

  公开（公告）日：2009-06-18

  Bicyclic heteroaryl-substituted imidazole compounds are described, which are useful as H 4 receptor modulators. Such compounds may be used in pharmaceutical compositions and methods for the modulation of histamine H 4 receptor activity and for the treatment of disease states, disorders, and conditions mediated by H 4 receptor activity, such as allergy, asthma, autoimmune diseases, and pruritis.

  描述了具有双环杂环芳基取代的咪唑化合物，这些化合物可用作H4受体调节剂。这种化合物可以用于制备药物组合物，用于调节组脊髓H4受体活性以及治疗由H4受体活性介导的疾病状态、紊乱和症状，例如过敏、哮喘、自身免疫疾病和瘙痒症。
• Structure–activity relationship studies of the chromosome segregation inhibitor, Incentrom A
  作者：Hee-Yoon Lee、Yongsik Jung、Wonyeob Kim、Jin Hee Kim、Min-Soo Suh、Seung Koo Shin、Hye-Joo Yoon

  DOI：10.1016/j.bmcl.2008.07.006

  日期：2008.8

  A series of Incentrom A analogs that inhibit the chromosome segregation process in yeast were synthesized and tested for their effects on chromosome stability and cell proliferation. Pharmacophore and structure-activity relationship of Incentrom A for the anti-yeast activity were established. (C) 2008 Elsevier Ltd. All rights reserved.
• Design and synthesis of novel sulfonamide-containing bradykinin hB2 receptor antagonists. Synthesis and structure-relationships of α,α-tetrahydropyranylglycine
  作者：Christopher I. Fincham、Alessandro Bressan、Piero D’Andrea、Alessandro Ettorre、Sandro Giuliani、Sandro Mauro、Stefania Meini、Marielle Paris、Laura Quartara、Cristina Rossi、Antonella Squarcia、Claudio Valenti、Fattori Daniela、Carlo Alberto Maggi

  DOI：10.1016/j.bmc.2012.01.036

  日期：2012.3

  A series of alpha,alpha-cycloalkylglycine sulfonamide compounds of general formula 1 has previously been identified by our group as selective human B-2(hB(2)) receptor antagonists. Here we report the in vitro and in vivo BK antagonist activity of a further evolution of the series, consisting in compounds of the general formula 2, containing either an alkyl piperazine or a 4-alkyl piperidine ring bearing various positively charged groups (R'). These studies unexpectedly revealed quite a flat nanomolar/subnanomolar SAR for the binding affinity, while differences were seen in the in vitro functional activities. We propose that variations in the residence time may explain these results. (C) 2012 Elsevier Ltd. All rights reserved.
• Discovery of a novel series of indoline carbamate and indolinylpyrimidine derivatives as potent GPR119 agonists
  作者：Kenjiro Sato、Hiromichi Sugimoto、Kentaro Rikimaru、Hiroshi Imoto、Masahiro Kamaura、Nobuyuki Negoro、Yoshiyuki Tsujihata、Hirohisa Miyashita、Tomoyuki Odani、Toshiki Murata

  DOI：10.1016/j.bmc.2014.01.028

  日期：2014.3

  GPR119 has emerged as an attractive target for anti-diabetic agents. We identified a structurally novel GPR119 agonist 22c that carries a 5-(methylsulfonyl) indoline motif as an early lead compound. To generate more potent compounds of this series, structural modifications were performed mainly to the central alkylene spacer. Installation of a carbonyl group and a methyl group on this spacer significantly enhanced agonistic activity, resulting in the identification of 2-[1-(5-ethylpyrimidin-2-yl)piperidin-4-yl] propyl 7-fluoro-5-(methylsulfonyl)-2,3-dihydro-1H-indole-1-carboxylate (20). To further expand the chemical series of indoline-based GPR119 agonists, several heterocyclic core systems were introduced as surrogates of the carbamate spacer that mimic the presumed active conformation. This approach successfully produced an indolinylpyrimidine derivative 37, 5-(methylsulfonyl)-1-[6-(1-[3-(propan-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-4-yl}oxy)pyrimidin-4-yl]-2,3-dihydro-1H-indole, which has potent GPR119 agonist activity. In rat oral glucose tolerance tests, these two indoline-based compounds effectively lowered plasma glucose excursion and glucose-dependent insulin secretion after oral administration. (C) 2014 Elsevier Ltd. All rights reserved.
• Design, synthesis of novel tryptophan derivatives for antiplatelet aggregation activity based on tripeptide pENW (pGlu-Asn-Trp)
  作者：Zhouling Xie、Sen Feng、Ying Wang、Chen Cao、Jing Huang、Yahui Chen、Yi Kong、Zhiyu Li

  DOI：10.1016/j.ejmech.2015.07.016

  日期：2015.9

  pENW, a three mer peptide derived from Agkistrodon acutus Guenther venom, has been found to be an antagonist of the GPIlb/IIIa receptor and shows antiplatelet aggregation activity. Based on pENW and a GPIIb/IIIa inhibitor Tirofiban, a series of tryptophan derivatives were designed, synthesized and evaluated for their antiplatelet aggregation activity induced by ADP. The most potent compound 87 was also tested for the bleeding time and antithrombotic activity in vivo in comparison with Tirofiban. The results indicated that 87 shows similar antiplatelet aggregation activity as Tirofiban to the aggregation of platelet induced by all of the four agonists, but has lower bleeding risk than Tirofiban, representing a promising lead compound for further study. (C) 2015 Elsevier Masson SAS. All rights reserved.