3-hydroxy-6',6'-dimethylpyrano[2',3':4,5]benzaldehyde | 246144-44-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-hydroxy-6',6'-dimethylpyrano[2',3':4,5]benzaldehyde
• 英文别名: 8-hydroxy-2,2-dimethyl-2H-chromene-6-carbaldehyde；8-hydroxy-2,2-dimethylchromene-6-carbaldehyde
• CAS: 246144-44-5
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: RMZUDHOOLRAWEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-6',6'-dimethylpyrano[2',3':4,5]benzaldehyde 在 盐酸 、 氢氧化钾 、 sodium acetate 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 丙酮 为溶剂， 反应 144.5h， 生成 3',5,7-trihydroxy-6",6"-dimethylpyrano[2",3":4',5']flavanonechalcone
  参考文献：
  名称：

  Hossain, M. Amzad, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 4, p. 427 - 430

  摘要：

  DOI：
• 作为产物：
  描述：

  3-氯-3-甲基-1-丁炔 、 3,4-二羟基苯甲醛 在 potassium carbonate 、 potassium iodide 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以1.22 g的产率得到3-hydroxy-6',6'-dimethylpyrano[2',3':4,5]benzaldehyde
  参考文献：
  名称：

  Hossain, M. Amzad, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 4, p. 427 - 430

  摘要：

  DOI：
• 作为试剂：
  描述：

  3-甲基-2-丁烯醛 、 3,4-二羟基苯甲醛 在 吡啶 、 3-hydroxy-6',6'-dimethylpyrano[2',3':4,5]benzaldehyde 、 silica gel 、 ethyl acetate n-hexane 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 3-hydroxy-6',6'-dimethylpyrano[2',3':4,5]benzaldehyde
  参考文献：
  名称：

  Hypoxia inducible factor-1 pathway inhibitors and uses as anticancer and imaging agents

  摘要：

  本公开涉及缺氧诱导因子-1途径抑制剂及其作为抗癌和成像剂的用途。在某些实施例中，本公开提供了所述的化合物和药物组合物。

  公开号：

  US09381260B2

文献信息

• HYPOXIA INDUCIBLE FACTOR-1 PATHWAY INHIBITORS AND USES AS ANTICANCER AND IMAGING AGENTS
  申请人：EMORY UNIVERSITY

  公开号：US20130164218A1

  公开（公告）日：2013-06-27

  This disclosure relates to Hypoxia Inducible Factor-1 pathway inhibitors and uses as anticancer and imaging agents. In certain embodiments, the disclosure contemplates compounds and pharmaceutical compositions disclosed herein.

  本公开涉及缺氧诱导因子-1通路抑制剂及其作为抗癌和成像剂的用途。在某些实施方式中，本公开考虑了在此披露的化合物和药物组成物。
• Design and in Vitro Activities of <i>N</i>-Alkyl-<i>N</i>-[(8-<i>R</i>-2,2-dimethyl-2<i>H</i>-chromen-6-yl)methyl]heteroarylsulfonamides, Novel, Small-Molecule Hypoxia Inducible Factor-1 Pathway Inhibitors and Anticancer Agents
  作者：Jiyoung Mun、Adnan Abdul Jabbar、Narra Sarojini Devi、Shaoman Yin、Yingzhe Wang、Chalet Tan、Deborah Culver、James P. Snyder、Erwin G. Van Meir、Mark M. Goodman

  DOI：10.1021/jm300752n

  日期：2012.8.9

  The hypoxia inducible factor (HIF) pathway is an attractive target for cancer, as it controls tumor adaptation to growth under hypoxia and mediates chemotherapy and radiation resistance. We previously discovered 3,4-dimethoxy-N-[(2,2-dimethyl-2H-chromen-6-yl)methyl]-N-phenylbenzenesulfonamide as a novel, small-molecule HIF-1 pathway inhibitor in a high-throughput cell-based assay, but its in vivo delivery is hampered by poor aqueous solubility (0.009 mu M in water; log P-7.4 = 3.7). Here we describe the synthesis of 12 N-alkyl-N-[(8-R-2,2-dimethyl-2H-chromen-6-yl)methyl]heteroarylsulfonamides, which were designed to possess optimal lipophilicities and aqueous solubilities by in silico calculations. Experimental log P-7.4 values of 8 of the 12 new analogs ranged from 1.2-3.1. Aqueous solubilities of three analogs were measured, among which the most soluble N-[(8-methoxy-2,2-dimethyl-2H-chromen-6-yl)methyl]-N-(propan-2-yl)pyridine-2-sulfonamide had an aqueous solubility of 80 mu M, e.g., a solubility improvement of similar to 9000-fold. The pharmacological optimization had limited impact on drug efficacy as the compounds retained IC50 values at or below 5 mu M in our HIF-dependent reporter assay.
• US9381260B2
  申请人：——

  公开号：US9381260B2

  公开（公告）日：2016-07-05
• Hossain, M. Amzad, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 4, p. 427 - 430
  作者：Hossain, M. Amzad

  DOI：——

  日期：——
• Hypoxia inducible factor-1 pathway inhibitors and uses as anticancer and imaging agents
  申请人：EMORY UNIVERSITY

  公开号：US09381260B2

  公开（公告）日：2016-07-05

  This disclosure relates to Hypoxia Inducible Factor-1 pathway inhibitors and uses as anticancer and imaging agents. In certain embodiments, the disclosure contemplates compounds and pharmaceutical compositions disclosed herein.

  本公开涉及缺氧诱导因子-1途径抑制剂及其作为抗癌和成像剂的用途。在某些实施例中，本公开提供了所述的化合物和药物组合物。