7-amino-4b,9b-dihydroxy-4bH-indeno[1,2-b]benzofuran-10(9bH)-one | 304689-01-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 7-amino-4b,9b-dihydroxy-4bH-indeno[1,2-b]benzofuran-10(9bH)-one
• 英文别名: 7-Amino-4b,9b-dihydroxyindeno[1,2-b][1]benzofuran-10-one
• CAS: 304689-01-8
• 化学式: C₁₅H₁₁NO₄
• 分子量: 269.257
• InChiKey: UIRDKOYKQMEGLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  92.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-amino-4b,9b-dihydroxy-4bH-indeno[1,2-b]benzofuran-10(9bH)-one 在 sodium periodate 作用下， 以 乙醇 为溶剂， 反应 0.25h， 生成 spiro[6-aminobenzofuran-2(3H),1'(3'H)-isobenzofuran]-3,3'-dione
  参考文献：
  名称：

  Efficient synthesis of 3 H ,3′ H -spiro[benzofuran-2,1′-isobenzofuran]-3,3′-dione as novel skeletons specifically for influenza virus type B inhibition

  摘要：

  An efficient and novel two step synthetic procedure to prepare various substituted 3H,3'H-spiro[benzofuran-2,1'-isobenzofuran]-3,3'-diones A, was established from very simple and easily available starting materials. The developed method is a robust and general approach for the synthesis of these structures. The prepared compounds were tested against influenza virus type A viz., A/Taiwan/1/86 (H1N1), A/Hong Kong/8/68 (H3N2) and type B viz., B/Panama/45/90, B/Taiwan/2/62, B/Lee/40, B/Brisbane/60/2008. Among 31 compounds tested, some of them showed good activity (selective index values >10) against these influenza viruses preferentially for type B. The most active compound 3b showed activity in 3.0-16.1 mu M range with a selectivity index value between 30 and 166 against these type B viruses, in which it was comparable to the antiviral agent favipiravir. Also, 3b is found to be inactive against other enveloped viruses (viz., HIV and HSV) showing its specificity for influenza viruses. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.015
• 作为产物：
  描述：

  水合茚三酮 、 3-氨基苯酚 在 溶剂黄146 作用下， 生成 7-amino-4b,9b-dihydroxy-4bH-indeno[1,2-b]benzofuran-10(9bH)-one
  参考文献：
  名称：

  Efficient synthesis of 3 H ,3′ H -spiro[benzofuran-2,1′-isobenzofuran]-3,3′-dione as novel skeletons specifically for influenza virus type B inhibition

  摘要：

  An efficient and novel two step synthetic procedure to prepare various substituted 3H,3'H-spiro[benzofuran-2,1'-isobenzofuran]-3,3'-diones A, was established from very simple and easily available starting materials. The developed method is a robust and general approach for the synthesis of these structures. The prepared compounds were tested against influenza virus type A viz., A/Taiwan/1/86 (H1N1), A/Hong Kong/8/68 (H3N2) and type B viz., B/Panama/45/90, B/Taiwan/2/62, B/Lee/40, B/Brisbane/60/2008. Among 31 compounds tested, some of them showed good activity (selective index values >10) against these influenza viruses preferentially for type B. The most active compound 3b showed activity in 3.0-16.1 mu M range with a selectivity index value between 30 and 166 against these type B viruses, in which it was comparable to the antiviral agent favipiravir. Also, 3b is found to be inactive against other enveloped viruses (viz., HIV and HSV) showing its specificity for influenza viruses. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.015

文献信息

• Efficient synthesis of 3 H ,3′ H -spiro[benzofuran-2,1′-isobenzofuran]-3,3′-dione as novel skeletons specifically for influenza virus type B inhibition
  作者：Yashwardhan Malpani、Raghavendra Achary、So Yeon Kim、Hee Chun Jeong、Pilho Kim、Soo Bong Han、Meehyein Kim、Chong-Kyo Lee、Jae Nyoung Kim、Young-Sik Jung

  DOI：10.1016/j.ejmech.2013.01.015

  日期：2013.4

  An efficient and novel two step synthetic procedure to prepare various substituted 3H,3'H-spiro[benzofuran-2,1'-isobenzofuran]-3,3'-diones A, was established from very simple and easily available starting materials. The developed method is a robust and general approach for the synthesis of these structures. The prepared compounds were tested against influenza virus type A viz., A/Taiwan/1/86 (H1N1), A/Hong Kong/8/68 (H3N2) and type B viz., B/Panama/45/90, B/Taiwan/2/62, B/Lee/40, B/Brisbane/60/2008. Among 31 compounds tested, some of them showed good activity (selective index values >10) against these influenza viruses preferentially for type B. The most active compound 3b showed activity in 3.0-16.1 mu M range with a selectivity index value between 30 and 166 against these type B viruses, in which it was comparable to the antiviral agent favipiravir. Also, 3b is found to be inactive against other enveloped viruses (viz., HIV and HSV) showing its specificity for influenza viruses. (C) 2013 Elsevier Masson SAS. All rights reserved.