2,6-dihydroxy-3-nitroacetophenone | 25205-34-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-dihydroxy-3-nitroacetophenone
• 英文别名: 1-(2,6-Dihydroxy-3-nitrophenyl)ethanone
• CAS: 25205-34-9
• 化学式: C₈H₇NO₅
• 分子量: 197.147
• InChiKey: KHGINYCMMLJGTB-UHFFFAOYSA-N

物化性质

• 熔点：
  119°C
• 沸点：
  276.4±40.0 °C(Predicted)
• 密度：
  1.520±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-dihydroxy-3-nitroacetophenone 在 吡啶 、 sodium benzoate 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 6-氨基-5-羟基-2-苯基色烯-4-酮
  参考文献：
  名称：

  α-Glucosidase inhibition of 6-hydroxyflavones. Part 3: Synthesis and evaluation of 2,3,4-trihydroxybenzoyl-containing flavonoid analogs and 6-aminoflavones as α-glucosidase inhibitors

  摘要：

  The SAR studies suggested that the C-ring of baicalein (1) was not necessary for the activity, and validated the importance of 2,3,4-trihydroxybenzoyl structure of 1. Thus, a series of 2,3,4-trihydroxybenzoyi-containing flavonoid analogs were investigated for the alpha-glucosidase inhibitory activity. The results indicated that 5,6,7-trihydroxy-2-phenyl-4-quinolone (2) and 5,6,7-trihydroxyflavanone (4) showed the comparable activity to 1, while 3,5,6,7-tetrahydroxyflavone (7), 5,6,7-trihydroxyisoflavone (8), and 6-hydroxygenistein (9) showed moderate alpha-glucosidase inhibitory activity. In addition, it was found that 6-amino-5,7-dihydroxyflavone (16) was a more potent and specific rat intestinal alpha-glucosidase inhibitor than 1, and showed the comparable activity to acarbose. This is the first report on mammalian intestinal alpha-glucosidase inhibitory activity of 6-aminoflavones. Kinetic studies revealed that 16 inhibited both sucrose- and maltose-hydrolyzing activities of rat intestinal alpha-glucosidase uncompetitively/ (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.010
• 作为产物：
  描述：

  2,6-二羟基苯乙酮 在 水 、 硝酸 作用下， 生成 2,6-dihydroxy-3-nitroacetophenone
  参考文献：
  名称：

  Naik et al., Proceedings - Indian Academy of Sciences, Section A, 1953, vol. 37, p. 765,768

  摘要：

  DOI：

文献信息

• 嘧啶并吡唑衍生物及其在医药上的用途
  申请人：中国药科大学

  公开号：CN117510505A

  公开（公告）日：2024-02-06

  本发明公开了一类嘧啶并吡唑衍生物及其在医药上的用途。所述嘧啶并吡唑衍生物为通式Ⅰ所示的化合物、其药学上可接受的盐或溶剂化物，#imgabs0#本发明的化合物可作为ALKBH5蛋白小分子抑制剂，在蛋白酶水平上抑制RNA去甲基化酶，可用于治疗急性白血病、肺癌、乳腺癌、结肠癌、前列腺癌、胰腺癌、胃癌、肝癌、卵巢癌、肾癌、神经胶质瘤、黑色素瘤、骨髓瘤、淋巴瘤、膀胱癌或宫颈癌。
• Synthesis and Biochemical Evaluation of a Series of Aminoflavones as Potential Inhibitors of Protein-Tyrosine Kinases p56lck, EGFr, and p60v-src
  作者：Mark Cushman、Helen Zhu、Robert L. Geahlen、Alan J. Kraker

  DOI：10.1021/jm00046a020

  日期：1994.9

  A series of nitroflavones, 8a-p, and their corresponding aminoflavone hydrochloride salts, 10a-p, was synthesized. The preparation of nitroflavones 8b-i,o,p began with commercially available o-hydroxyacetophenones 2b-f which were converted to o-hydroxynitroacetophenones 3a-h via a variety of nitration methods, followed by condensation with nitrobenzoyl chlorides and cyclization under acidic condition. The nitroflavones 8aj-n were prepared by nitration of the corresponding flavones 7a-e. These new compounds were evaluated for their abilities to inhibit the in. vitro protein-tyrosine kinase activities of p56(1ck), EGFr, and p60(v-src), and all of the active compounds were amino-substituted flavones. None of the nitroflavones inhibited the enzymes. The most active substance in this series against p56(lck) was compound 10j, which had an IC50 of is mu M. When tested versus EGFr, compounds 10a,m displayed IC50's of 8.7 and 7.8 mu M, respectively. Against p60(v-src), 10a,m showed IC50 values of 28.8 and 38.4 mu M, respectively.
• Joshi et al., Journal of the Indian Chemical Society, 1959, vol. 36, p. 59,61, 63
  作者：Joshi et al.

  DOI：——

  日期：——
• Naik; Thakor, Proceedings - Indian Academy of Sciences, Section A, 1953, # 37, p. 774,777
  作者：Naik、Thakor

  DOI：——

  日期：——
• Amin et al., Journal of the Indian Chemical Society, 1959, vol. 36, p. 833,835
  作者：Amin et al.

  DOI：——

  日期：——