3-methyl-4-(4-methylphenyl)-1,2-oxazol-5-amine | 925007-44-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-methyl-4-(4-methylphenyl)-1,2-oxazol-5-amine
• CAS: 925007-44-9
• 化学式: C₁₁H₁₂N₂O
• 分子量: 188.229
• InChiKey: KWAOIMTYDDQVOO-UHFFFAOYSA-N

物化性质

• 沸点：
  326.4±30.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methyl-4-(4-methylphenyl)-1,2-oxazol-5-amine 在 氯磺酸 、 氯化亚砜 、 三甲胺 作用下， 以 乙腈 为溶剂， 反应 17.0h， 生成 N-[3-methyl-4-(4-methyl-3-sulfamoylphenyl)-1,2-oxazol-5-yl]acetamide
  参考文献：
  名称：

  Human carbonic anhydrase inhibitory profile of mono- and bis-sulfonamides synthesized via a direct sulfochlorination of 3- and 4-(hetero)arylisoxazol-5-amine scaffolds

  摘要：

  Three distinct series of isoxazole-based primary mono- and bis-sulfonamides have been synthesized via direct sulfochlorination, each of them delivering nanomolar inhibitors of human carbonic anhydrase. Certain pronounced SAR trends have been established and rationalized by in silico docking. These findings expand the structure-activity knowledge base for heterocycle-containing sulfonamide carbonic anhydrase inhibitors and further validate the power of direct electrophilic sulfochlorination as a means of introducing the pharmacophoric primary sulfonamide group into structurally diverse aromatic precursors. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.02.018
• 作为产物：
  描述：

  1-(p-methylphenyl)-1-cyanoacetone 在 羟胺 、 sodium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以91%的产率得到3-methyl-4-(4-methylphenyl)-1,2-oxazol-5-amine
  参考文献：
  名称：

  Human carbonic anhydrase inhibitory profile of mono- and bis-sulfonamides synthesized via a direct sulfochlorination of 3- and 4-(hetero)arylisoxazol-5-amine scaffolds

  摘要：

  Three distinct series of isoxazole-based primary mono- and bis-sulfonamides have been synthesized via direct sulfochlorination, each of them delivering nanomolar inhibitors of human carbonic anhydrase. Certain pronounced SAR trends have been established and rationalized by in silico docking. These findings expand the structure-activity knowledge base for heterocycle-containing sulfonamide carbonic anhydrase inhibitors and further validate the power of direct electrophilic sulfochlorination as a means of introducing the pharmacophoric primary sulfonamide group into structurally diverse aromatic precursors. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.02.018

文献信息

• PHARMACEUTICAL COMPOUND
  申请人：IOmet Pharma Ltd.

  公开号：US20170267668A1

  公开（公告）日：2017-09-21

  Provided is a tryptophan-2,3-dioxygenase (TDO) and/or indoleamine-2,3-dioxygenase (IDO) inhibitor compound for use in medicine, which compound comprises the following formula (I): wherein X 1 is selected from C and N; X 3 and X 5 may be the same or different and each is independently selected from C, N, O and S; Y is selected from N and O; Z is selected from C, N and O; each bond represented by a dotted line may independently be a double bond or a single bond, provided that valencies at each ring atom are maintained and provided that the ring Q contains at least one double bond and provided that the atom N has a double bond; R 3 and R 5 may be present or absent and may be the same or different and each is independently selected from H and a substituted or unsubstituted organic group, provided that the number of R 3 groups present is such that the valency of X 3 is maintained, and the number of R 5 groups present is such that the valency of X 5 is maintained; each R 11 and R 12 may be present or absent and may be the same or different and each is independently selected from H and a substituted or unsubstituted organic group, provided that the number of R 11 and R 12 groups present is such that the valency of Z is maintained; R 21 is selected from H and a substituted or unsubstituted organic group; R 22 may be present or absent and is selected from H and a substituted or unsubstituted organic group; and Cy is a cyclic organic group.