1-(3-hydroxyphenyl)-2-phenylethanone | 332072-68-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-(3-hydroxyphenyl)-2-phenylethanone
• 英文别名: 3-hydroxyphenyl benzyl ketone
• CAS: 332072-68-1
• 化学式: C₁₄H₁₂O₂
• 分子量: 212.248
• InChiKey: GXTPGWKRTVGUHN-UHFFFAOYSA-N

物化性质

• 熔点：
  97-98 °C
• 沸点：
  396.6±25.0 °C(Predicted)
• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(氯甲基)-5-甲基-2-[4-(三氟甲基)苯基]-1,3-噁唑 、 1-(3-hydroxyphenyl)-2-phenylethanone 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 1-[3-[[5-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]methoxy]phenyl]-2-phenylethanone
  参考文献：
  名称：

  New Azolidinediones as Inhibitors of Protein Tyrosine Phosphatase 1B with Antihyperglycemic Properties

  摘要：

  Insulin resistance in the liver and peripheral tissues together with a pancreatic cell defect are the common causes of type 2 diabetes. It is now appreciated that insulin resistance can result from a defect in the insulin receptor signaling system, at a site post binding of insulin to its receptor. Protein tyrosine phosphatases (PTPases) have been shown to be negative regulators of the insulin receptor. Inhibiton of PTPase may be an effective method in the treatment of type 2 diabetes. A series of azolidinediones has been prepared as protein tyrosine phosphatase 1B (PTP1B) inhibitors. Several compounds were potent inhibitors against the recombinant rat and human PTP1B enzymes with submicromolar IC50 values. Elongated spacers between the azolidinedione moiety and the central aromatic portion of the molecule as well as hydrophobic groups at the vicinity of this aromatic region were very important to the inhibitory activity. Oxadiazolidinediones 87 and 88 and the corresponding acetic acid analogues 119 and 120 were the best h-PTP1B inhibitors with IC50 values in the range of 0.12-0.3 mu M. Several compounds normalized plasma glucose and insulin levels in the ob/ob and db/db diabetic mouse models.

  DOI：

  10.1021/jm990476x
• 作为产物：
  描述：

  苯乙酸 、 间羟基苯甲酸 在 Iron(II,III) oxide nanopowder 作用下， 以27%的产率得到1-(3-hydroxyphenyl)-2-phenylethanone
  参考文献：
  名称：

  磁铁矿纳米颗粒催化芳基和烷基羧酸的脱羧交叉酮化

  摘要：

  在催化量的磁铁矿纳米粉的存在下，芳族和脂族羧酸的混合物被选择性地转化为相应的芳基烷基酮。作为副产品，仅释放二氧化碳和水。这种催化的交叉酮化可以使芳族系统进行区域选择性酰化，因此，它是Friedel-Crafts酰化反应的可持续替代方案。

  DOI：

  10.1002/adsc.201000429

文献信息

• [EN] NOVEL DIHYDROPYRIMIDIN-2(1H)-ONE COMPOUNDS AS S-NITROSOGLUTATHIONE REDUCTASE INHIBITORS<br/>[FR] NOUVEAUX COMPOSÉS DIHYDROPYRIMIDINE-2(1H)-ONES EN TANT QU'INHIBITEURS DE LA S-NITROSOGLUTATHION RÉDUCTASE
  申请人：N30 PHARMACEUTICALS LLC

  公开号：WO2011038204A1

  公开（公告）日：2011-03-31

  The present invention is directed to novel dihydropyrimidin-2(1H)-one compounds useful as S-nitrosoglutathione reductase (GSNOR) inhibitors, pharmaceutical compositions comprising such compounds, and methods of making and using the same.

  本发明涉及一种新型二氢嘧啶-2(1H)-酮化合物，可用作S-亚硝基谷胱甘肽还原酶（GSNOR）抑制剂，包括这些化合物的药物组合物，以及制备和使用这些化合物的方法。
• FUSED HETEROCYCLIC COMPOUND
  申请人：Ishikawa Tomoyasu

  公开号：US20100216788A1

  公开（公告）日：2010-08-26

  The present invention provides a compound represented by the formula: wherein R 1a is a hydrogen atom, R 2a is a C 1-6 alkyl group substituted by a group represented by —NR 6a —CO—(CH 2 ) n —SO 2 — optionally halogenated C 1-4 alkyl wherein n is an integer of 1 to 4, R 6a is a hydrogen atom or a C 1-4 alkyl group, and —(CH 2 ) n — is optionally substituted by C 1-4 alkyl, R 3a is a hydrogen atom or a C 1-6 alkyl group, R 4a is a halogen atom or a C 1-6 alkyl group, R 5a is a halogen atom or a C 1-6 alkyl group, and X a is a hydrogen atom or a halogen atom, or a salt thereof. The compound of the present invention has a superior tyrosine kinase inhibitory action, is highly safe, and is sufficiently satisfactory as a pharmaceutical product.

  本发明提供了一种化合物，其表示为以下式子：其中，R1a是氢原子，R2a是一个C1-6烷基，被一个表示为—NR6a—CO—（CH2）n—SO2—的基团取代，该基团可选地卤代C1-4烷基，其中n是1至4的整数，R6a是氢原子或C1-4烷基，—（CH2）n—可选地被C1-4烷基取代，R3a是氢原子或C1-6烷基，R4a是卤原子或C1-6烷基，R5a是卤原子或C1-6烷基，Xa是氢原子或卤原子，或其盐。本发明的化合物具有卓越的酪氨酸激酶抑制作用，高度安全，并且作为药物产品完全令人满意。
• Novel Dihydropyrimidin-2(1H)-one Compounds as S-Nitrosoglutathione Reductase Inhibitors
  申请人：Sun Xicheng

  公开号：US20120208817A1

  公开（公告）日：2012-08-16

  The present invention is directed to novel dihydropyrimidin-2(1H)-one compounds useful as S-nitrosoglutathione reductase (GSNOR) inhibitors, pharmaceutical compositions comprising such compounds, and methods of making and using the same.

  本发明涉及一种新型二氢嘧啶-2(1H)-酮化合物，其可用作S-亚硝基谷胱甘肽还原酶（GSNOR）抑制剂，包括这种化合物的制药组合物，以及制造和使用它们的方法。
• Dihydropyrimidin-2(1H)-one compounds as S-nitrosoglutathione reductase inhibitors
  申请人：N30 Pharmaceuticals, Inc.

  公开号：US09067893B2

  公开（公告）日：2015-06-30

  The present invention is directed to novel dihydropyrimidin-2(1H)-one compounds useful as S-nitrosoglutathione reductase (GSNOR) inhibitors, pharmaceutical compositions comprising such compounds, and methods of making and using the same.

  本发明涉及一种新型二氢嘧啶-2(1H)-酮化合物，可用作S-亚硝基谷胱甘肽还原酶(GSNOR)抑制剂，包括这种化合物的制药组合物以及制备和使用它们的方法。
• Process for the preparation of arylalkylamines and substituted arylalkylamines
  申请人：HOECHST CELANESE CORPORATION

  公开号：EP0481705A1

  公开（公告）日：1992-04-22

  Arylalkylamines (as a sulfate salt) e.g. tyramine sulfate, are prepared by reacting substituted or unsubstituted arylalkylketones with a lower alkylnitrite in the presence of hydrogen chloride in a dipolar aprotic solvent, then combining the reaction mixture with water and extracting it with a lower alkyl ester or alcohol to recover an aryl-α-oximinoalkylketone extract. The extract, combined with a supported hydrogenation catalyst (e.g. palladium on carbon) in a nonaqueous reaction medium of a major proportion of a mildly protic carboxylic acid (e.g. acetic acid) and a minor proportion of a srong inorganic acid (e.g. sulfuric acid), which is effective in the presence of the catalyst for secondary alcohol dehydration and active as an absorbant for water produced in the dehydration reaction, is hydrogenated to produce the arylalkylamine sulfate sale.

  芳烷基胺（作为硫酸盐），例如硫酸酪胺，是通过在氯化氢存在下，在二极性非 普罗溶剂中，使取代或未取代的芳烷基酮与低级亚硝酸烷基酯反应，然后将反应混 合物与水混合，并用低级烷基酯或醇萃取，以回收芳基-α-氧亚氨基烷基酮萃取物。该萃取物与支撑氢化催化剂（如碳上钯）在非水反应介质中结合，该反应介质主要成分为轻度质子羧酸（如乙酸），次要成分为强无机酸（如硫酸），在催化剂存在下，强无机酸对二次醇脱水有效，对脱水反应中产生的水有吸附作用，氢化反应生成出售的芳基烷基胺硫酸盐。