5-(tert-butoxycarbonylaminomethyl)-1,3,4-oxadiazol-2(3H)-one | 1046079-09-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(tert-butoxycarbonylaminomethyl)-1,3,4-oxadiazol-2(3H)-one
• 英文别名: (5-oxo-4,5-dihydro-[1,3,4]oxadiazol-2-ylmethyl)-carbamic acid tert-butyl ester；tert-butyl N-[(2-oxo-3H-1,3,4-oxadiazol-5-yl)methyl]carbamate
• CAS: 1046079-09-7
• 化学式: C₈H₁₃N₃O₄
• 分子量: 215.209
• InChiKey: CEDKBIHOXKHDKL-UHFFFAOYSA-N

物化性质

• 熔点：
  131 °C
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  89
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(tert-butoxycarbonylaminomethyl)-1,3,4-oxadiazol-2(3H)-one 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 以88%的产率得到5-(aminomethyl)-1,3,4-oxadiazol-2(3H)-one hydrochloride
  参考文献：
  名称：

  GABAA 受体激动剂的合成及其在 GABA 结合位点中的 α 亚基选择性和方向的评估。

  摘要：

  用于治疗各种疾病的药物靶向 GABA A 受体。为了开发 α 亚基选择性化合物，我们合成了 5-(4-哌啶基)-3-异恶唑醇 (4-PIOL) 衍生物。3-isoxazolol 部分被 1,3,5-oxadiazol-2-one、1,3,5-oxadiazol-2-thione 和取代的 1,2,4-triazol-3-ol 杂环取代碱性哌啶取代基以及不含碱性氮的取代基。通过 [(3) H] muscimol 绑定和膜片钳实验与异源表达 GABA A α ibeta 3gamma 2 受体 (i = 1-6) 筛选化合物。5-aminomethyl-3 H-[1,3,4]oxadiazol-2-one 5d 的作用与 GABA 对所有 α 亚基亚型的影响相当。5-哌啶-4-基-3 H-[1,3,4]恶二唑-2-one 5a和5-哌啶-4-yl-3 H-[1,3,4]恶二唑-2-硫酮6a分别为α

  DOI：

  10.1021/jm701562x
• 作为产物：
  描述：

  N-BOC-甘氨酸乙酯 在 一水合肼 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 5-(tert-butoxycarbonylaminomethyl)-1,3,4-oxadiazol-2(3H)-one
  参考文献：
  名称：

  (S)-2-Amino-3-(5-methyl-3-hydroxyisoxazol-4-yl)propanoic Acid (AMPA) and Kainate Receptor Ligands: Further Exploration of Bioisosteric Replacements and Structural and Biological Investigation

  摘要：

  Starting from 1-4 and 7 structural templates, analogues based on bioisosteric replacements (5a-c vs 1, 2 and 6 vs 7) were synthesized for completing the SAP. analysis. Interesting binding properties at GluA2, G1uK1, and G1uK3 receptors were discovered. The requirements for G1uK3 interaction were elucidated by determining the X-ray structures of the GluK3-LBD with 2 and Sc and by computational studies. Antinociceptive potential was demonstrated for GluK1 partial agonist 3 and antagonist 7 (2 mg/kg ip).

  DOI：

  10.1021/acs.jmedchem.8b00099

文献信息

• [EN] SUBSTITUTED NAPHTHYRIDINES AND THEIR USE AS SYK KINASE INHIBITORS<br/>[FR] NAPHTYRIDINES SUBSTITUÉES ET LEUR UTILISATION COMME INHIBITEURS DE SYK KINASE
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2011092128A1

  公开（公告）日：2011-08-04

  The invention relates to new substituted naphthyridines of formula (1), as well as pharmacologically acceptable salts, diastereomers, enantiomers, racemates, hydrates or solvates thereof, wherein R1 is selected from among -O-R3 or -NR3R4, R3 is C1-6-alkyl which is substituted by R5 and R6 R5 is selected from hydrogen, branched or linear C1-6-alkyl, C2-6-alkenyl, -C1-6-alkylen-O-C1-3-alkyl, C1-3-haloalkyl, R6 is ring X wherein n is either 0 or 1, and Formula (I) is a either a single or a double bond and wherein A, B, D and E are each independently from one another selected from CH2, CH, C, N, NH, O or S and wherein ring X is attached to the molecule either via position A, B, D or E, wherein said ring X may optionally be further substituted by one, two or three residues each selected individually from the group consisting of -oxo, hydroxy, -C1-3-alkyl, -C1-3-haloalkyl, -O-C1-3-alkyl, -C1-3-alkanol and halogen, and wherein R4, R2, R7, R8, R9, R10, R11 and Q may have the meanings as given in claim 1, as well as pharmaceutical compositions containing these compounds.

  该发明涉及公式（1）的新取代萘啉衍生物，以及其药理学上可接受的盐、对映体、非对映体异构体、立体异构体、水合物或溶剂化合物，其中R1从-O-R3或-NR3R4中选择，R3是C1-6-烷基，其被R5和R6取代，R5从氢、支链或直链C1-6-烷基、C2-6-烯基、-C1-6-烷基-氧-C1-3-烷基、C1-3-卤代烷基中选择，R6是环X，其中n为0或1，公式（I）为单键或双键，其中A、B、D和E分别独立地从CH2、CH、C、N、NH、O或S中选择，环X通过位置A、B、D或E连接到分子上，其中所述环X可以选择性地进一步被一个、两个或三个残基取代，每个残基分别从-氧化物、羟基、-C1-3-烷基、-C1-3-卤代烷基、-O-C1-3-烷基、-C1-3-醇基和卤素组成的群中选择，R4、R2、R7、R8、R9、R10、R11和Q的含义可以如权利要求1中所述，以及含有这些化合物的药物组合物。
• SUBSTITUTED NAPHTHYRIDINES AND THEIR USE AS MEDICAMENTS
  申请人：Hoffmann Matthias

  公开号：US20120028939A1

  公开（公告）日：2012-02-02

  The invention relates to new substituted naphthyridines of formula 1, as well as pharmacologically acceptable salts, diastereomers, enantiomers, racemates, hydrates or solvates thereof, wherein R 1 is selected from among —O—R 3 or —NR 3 R 4 , R 3 is C 1-6 -alkyl which is substituted by R 5 and R 6 , R 5 is selected from hydrogen, branched or linear C 1-6 -alkyl, C 2-6 -alkenyl, —C 1-6 -alkylen-O—C 1-3 -alkyl, C 1-3 -haloalkyl, R 6 is ring X wherein n is either 0 or 1, and is a either a single or a double bond and wherein A, B, D and E are each independently from one another selected from CH 2 , CH, C, N, NH, O or S and wherein ring X is attached to the molecule either via position A, B, D or E, wherein said ring X may optionally be further substituted by one, two or three residues each selected individually from the group consisting of -oxo, hydroxy, —C 1-3 -alkyl, —C 1-3 -haloalkyl, —O—C 1-3 -alkyl, —C 1-3 -alkanol and halogen, and wherein R 4 , R 2 , R 7 , R 8 , R 9 , R 10 , R 11 and Q may have the meanings as given in claim 1, as well as pharmaceutical compositions containing these compounds.

  该发明涉及公式1的新取代萘啉类化合物，以及其药理学上可接受的盐、对映体、旋光异构体、消旋体、水合物或溶剂合物，其中R1从—O—R3或—NR3R4中选择，R3是经R5和R6取代的C1-6烷基，R5从氢、支链或直链C1-6烷基、C2-6烯基、—C1-6烷基氧基-C1-3烷基、C1-3卤代烷基中选择，R6是环X，其中n为0或1，为单键或双键，A、B、D和E各自独立地从CH2、CH、C、N、NH、O或S中选择，环X通过位置A、B、D或E连接到分子，所述环X可以选择地进一步由氧代、羟基、—C1-3烷基、—C1-3卤代烷基、—O—C1-3烷基、—C1-3烷醇和卤素中的每个单独选择的一个、两个或三个残基取代，并且R4、R2、R7、R8、R9、R10、R11和Q可以具有如权利要求1中所给出的含义，以及含有这些化合物的药物组合物。
• SUBSTITUTED NAPHTHYRIDINES AND THEIR USE AS SYK KINASE INHIBITORS
  申请人：Boehringer Ingelheim International GmbH

  公开号：EP2528915A1

  公开（公告）日：2012-12-05
• US8969568B2
  申请人：——

  公开号：US8969568B2

  公开（公告）日：2015-03-03
• US9187478B2
  申请人：——

  公开号：US9187478B2

  公开（公告）日：2015-11-17