N-isopropyl-benzo[d]oxazole-2-carboxamide | 27383-73-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: N-isopropyl-benzo[d]oxazole-2-carboxamide
• 英文别名: Benzoxazole-2-carboxylic acid isopropyl-amide；benzooxazole-2-carboxylic acid isopropylamide；N-propan-2-yl-1,3-benzoxazole-2-carboxamide
• CAS: 27383-73-9
• 化学式: C₁₁H₁₂N₂O₂
• 分子量: 204.228
• InChiKey: KRDOPTYJCJHYRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  异丙胺 、 苯并[d]噁唑-2-羧酸甲酯 生成 N-isopropyl-benzo[d]oxazole-2-carboxamide
  参考文献：
  名称：

  Dickore,K. et al., Justus Liebigs Annalen der Chemie, 1970, vol. 733, p. 70 - 87

  摘要：

  DOI：

文献信息

• S₈-Catalyzed triple cleavage of bromodifluoro compounds for the assembly of N-containing heterocycles
  作者：Shuilin Deng、Haohua Chen、Xingxing Ma、Yao Zhou、Kai Yang、Yu Lan、Qiuling Song

  DOI：10.1039/c9sc01333d

  日期：——

  cleavage of three C–X bonds, including two inert C(sp3)–F bonds on bromodifluoroacetamides, while leaving C–C bonds intact. This strategy will undoubtedly further consummate the role of halo difluoro compounds and enrich both fluorine chemistry and pharmaceutical sciences.

  首次公开了空前的S 8催化的溴二氟乙酰胺的选择性三裂解。在该策略中，以级联方案以良好或优异的产率获得了有价值的2-酰胺基取代的苯并咪唑，苯并恶唑和苯并噻唑。机理研究表明，通过选择性裂解三个溴二氟乙酰胺上的三个C–X键（包括两个惰性C（sp 3）–F键）原位生成C2源，而保持C–C键完整。无疑，该策略将进一步完善卤代二氟化合物的作用，并丰富氟化学和制药科学。
• Discovery of a Novel Class of Negative Allosteric Modulator of the Dopamine D₂ Receptor Through Fragmentation of a Bitopic Ligand
  作者：Shailesh N. Mistry、Jeremy Shonberg、Christopher J. Draper-Joyce、Carmen Klein Herenbrink、Mayako Michino、Lei Shi、Arthur Christopoulos、Ben Capuano、Peter J. Scammells、J. Robert Lane

  DOI：10.1021/acs.jmedchem.5b00585

  日期：2015.9.10

  Recently, we have demonstrated that N-((trans)-4-(2-(7-cyano-3,4-dihydroisoquinolin-2(1H)-yl)-ethyl)cyclohexyl)-1H-indole-2-carboxamide (0269652) (1) adopts a bitopic pose at one protomer of a dopamine D-2 receptor (D2R) dimer to negatively modulate the binding of dopamine at the other protomer. The 1H-indole-2-carboxamide moiety of 1 extends into a secondary pocket between the extracellular ends of TM2 and TM7 within the D2R protomer. To target this putative allosteric site, we generated and characterized fragments that include and extend from the 1H-indole-2-carboxamide moiety of 1. N-Isopropyl-1H-indole-2-carboxamide (3) displayed allosteric pharmacology and sensitivity to mutations of the same residues at the top of TM2 as was observed for 1. Using 3 as an "allosteric lead", we designed and synthesized an extensive fragment library to generate novel SAR and identify N-butyl-1H-indole-2-carboxamide (11d), which displayed both increased negative cooperativity and affinity for the D2R. These data illustrate that fragmentation of extended compounds can expose fragments with purely allosteric pharmacology.
• COMPOUNDS, COMPOSITIONS AND METHODS
  申请人：Denali Therapeutics Inc.

  公开号：US20220177438A1

  公开（公告）日：2022-06-09

  The present disclosure relates generally to eukaryotic initiation factor 2B modulators, or a pharmaceutically acceptable salt, stereoisomer, mixture of stereoisomers, or prodrug thereof, and methods of making and using thereof.
• Dickore,K. et al., Justus Liebigs Annalen der Chemie, 1970, vol. 733, p. 70 - 87
  作者：Dickore,K. et al.

  DOI：——

  日期：——