5-tert-butyl-3-(N-methylcarbamoyl)-1,2,4-oxadiazole | 918814-26-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-tert-butyl-3-(N-methylcarbamoyl)-1,2,4-oxadiazole
• 英文别名: 5-tert-Butyl-N-methyl-1,2,4-oxadiazole-3-carboxamide；5-tert-butyl-N-methyl-1,2,4-oxadiazole-3-carboxamide
• CAS: 918814-26-3
• 化学式: C₈H₁₃N₃O₂
• 分子量: 183.21
• InChiKey: FMGZRTXEEFXQSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  68
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(2,2-dimethylpropanoyl)oxyimino-2-amino-N-methylacetamide 在 四丁基氟化铵 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以93%的产率得到5-tert-butyl-3-(N-methylcarbamoyl)-1,2,4-oxadiazole
  参考文献：
  名称：

  Facile Synthesis of 3-Carbamoyl-1,2,4-Oxadiazoles

  摘要：

  通过三个步骤，从2-甲基-4-硝基异恶唑啉-5(2H)-酮合成了1,2,4-噁二唑系列，该系列在3位具有氨基甲酰基。 硝基异恶唑酮的氨解反应以极高的产率生成2-氨基-2-羟基亚氨基-N-甲基乙酰胺。 该关键酰胺肟的O-酰化反应，以及随后的环合反应，进展顺利，生成3-氨基甲酰基-1,2,4-噁二唑，其5位具有取代基，可通过改变O-酰化剂轻松进行修饰。 由于每个步骤只需要简单的操作，因此该方法的合成实用性很高。

  DOI：

  10.1055/s-2006-950210

文献信息

• ARYL HYDROCARBON RECEPTOR MODULATOR
  申请人：Ariagen, Inc.

  公开号：US20190307731A1

  公开（公告）日：2019-10-10

  Disclosed is an aryl hydrocarbon receptor modulator of formula (I), and a pharmaceutically acceptable salt thereof, wherein R′ is H, CN, CH 2 (OH)R 0 , C m H 2m+1 , C n H 2n-1 , C n H 2n-3 , two R a are independently H or two R a together form ═O or ═N—W 3 —R 1 ; A is a C 6 to C 10 aromatic ring unsubstituted or substituted with 1 to 3 R, or a C 2 -C 10 heteroaromatic ring interrupted by 1 to 5 heteroatoms selected from N, O, and S or a 4 to 7 membered nonaromatic heterocyclic ring containing C═N and interrupted by 1 to 3 heteroatoms selected from N, O, and S, with either one unsubstituted or substituted with 1 to 3 R; Q is R, or is a C 6 to C 10 aromatic ring or a C 2 to C 10 heteroaromatic ring unsubstituted or substituted with 1 to 3 R and interrupted by 1 to 5 heteroatoms selected from N, O, and S; and R is R c which is C-attached or R N which is N-attached. The compounds of formula (I) of the present invention can regulate AhR activity, and can be used to inhibit the growth of cancer cells and inhibit the metastasis and invasion of tumor cells.

  本发明揭示了一种化学式（I）的芳香烃受体调节剂及其药用可接受盐，其中R′为H、CN、CH2（OH）R0、CmH2m+1、CnH2n-1、CnH2n-3，两个Ra独立地为H或两个Ra共同形成═O或═N—W3—R1；A为未取代或取代1至3个R的C6至C10芳香环，或由N、O和S中选择的1至5个杂原子中断的C2-C10杂芳环，或含有C═N并由N、O和S中选择的1至3个杂原子中断的4至7个成员的非芳杂环，其中一个未取代或取代1至3个R；Q为R，或者是未取代或取代1至3个R并由N、O和S中断的C6至C10芳香环或C2至C10杂芳环；R为C-连接的Rc或N-连接的RN。本发明的化合物可以调节AhR活性，可用于抑制癌细胞的生长，以及抑制肿瘤细胞的转移和侵袭。
• Inverse electron-demand 1,3-dipolar cycloaddition of nitrile oxide with common nitriles leading to 3-functionalized 1,2,4-oxadiazoles
  作者：Nagatoshi Nishiwaki、Kazuya Kobiro、Shotaro Hirao、Jun Sawayama、Kazuhiko Saigo、Yumiko Ise、Yoshikazu Okajima、Masahiro Ariga

  DOI：10.1039/c1ob05682d

  日期：——

  A carbamoyl-substituted nitrile oxide was generated upon treatment of easily available 2-methyl-4-nitro-3-isoxazolin-5(2H)-one with THF (not dried); the reaction proceeded efficiently even in the absence of any special reagents and reaction conditions. The nitrile oxide caused 1,3-dipolar cycloaddition with common aliphatic nitriles or electron-rich aromatic nitriles to afford 3-functionalized 1,2

  处理易得的2-甲基-4-硝基-3-异恶唑啉-5（2 H）-四氢呋喃（未干燥）; 即使没有任何特殊的试剂和反应条件，反应也能有效地进行。一氧化氮与常见的脂肪族腈或富电子芳族腈引起1,3-偶极环加成反应，生成3-官能化的1,2,4-恶二唑，它们有望用作制备各种功能性材料的前体，方法是氨基甲酰基的化学转化。传统的1,2,4-恶二唑制备方法包括将富电子腈与缺电子腈或被路易斯酸活化的腈环加成，而我们的方法采用了富电子腈与缺电子的一氧化氮-逆电子需求的1,3-环加成。
• HETEROARYL COMPOUNDS AS BTK INHIBITORS AND USES THEREOF
  申请人：Merck Patent GmbH

  公开号：US20160096834A1

  公开（公告）日：2016-04-07

  The present invention relates to imidazo pyridine compounds, and pharmaceutically acceptable compositions thereof, useful as BTK inhibitors.

  本发明涉及咪唑吡啶化合物及其药学上可接受的组合物，用作BTK抑制剂。
• ARYL HYDROCARBON RECEPTOR MODULATORS
  申请人：SHENZHEN IMMUNOVA PHARMACEUTICAL CO., LTD.

  公开号：US20190330201A1

  公开（公告）日：2019-10-31

  The disclosure discloses an aryl hydrocarbon receptor modulators of formula (I), and pharmaceutically acceptable salts, R′ is H, CN, CH 2 (OH)R 0 , C m H 2m+1 , C n H 2n-1 , C n H 2n-3 , two R a is independently H, or two R a together form ═O or ═N—W 3 —R 1 ; A is a C 6 to C 10 aromatic ring, or a C 2 to C 10 heteroaromatic ring containing 1 to 5 heteroatom from N, O and S, or 4 to 7 membered non-aromatic heterocyclic ring containing 1 to 3 heteroatom from N, O and S and C═N, which are with no substituent or substituted by 1 or 3 R; Q is R, or a C 6 to C 10 aromatic ring or a C 2 to C 10 heteroaromatic ring containing 1 to 5 heteroatom selected from N, O and S, which are with no substituent or substituted by 1 or 3 R; R is R c connected with C or R N connected with N.
• [EN] HETEROARYL COMPOUNDS AS BTK INHIBITORS AND USES THEREOF<br/>[FR] COMPOSÉS HÉTÉROARYLE SERVANT D'INHIBITEURS DE LA BTK, ET LEURS UTILISATIONS
  申请人：MERCK PATENT GMBH

  公开号：WO2016057500A1

  公开（公告）日：2016-04-14

  The present invention relates to imidazopyridine compounds of formula I, and pharmaceutically acceptable compositions thereof, useful as BTK inhibitors.