1,12-Dihydroxy-11-oxapentacyclo[10.7.0.02,10.04,8.013,18]nonadeca-2(10),3,8,13,15,17-hexaen-19-one | 1416230-81-3

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 1,12-Dihydroxy-11-oxapentacyclo[10.7.0.02,10.04,8.013,18]nonadeca-2(10),3,8,13,15,17-hexaen-19-one
• 英文别名: 1,12-dihydroxy-11-oxapentacyclo[10.7.0.02,10.04,8.013,18]nonadeca-2(10),3,8,13,15,17-hexaen-19-one
• CAS: 1416230-81-3
• 化学式: C₁₈H₁₄O₄
• 分子量: 294.307
• InChiKey: ALKGTCWQYVQBBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,12-Dihydroxy-11-oxapentacyclo[10.7.0.02,10.04,8.013,18]nonadeca-2(10),3,8,13,15,17-hexaen-19-one 在 碘 作用下， 以 乙醇 为溶剂， 以70%的产率得到spiro[2-benzofuran-3,2'-6,7-dihydro-5H-cyclopenta[f][1]benzofuran]-1,3'-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 、 5-茚醇 在 溶剂黄146 作用下， 生成 1,12-Dihydroxy-11-oxapentacyclo[10.7.0.02,10.04,8.013,18]nonadeca-2(10),3,8,13,15,17-hexaen-19-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

• INDANONE DERIVATIVES, PHARMACEUTICALLY ACCEPTABLE SALTS OR OPTICAL ISOMERS THEREOF, PREPARATION METHOD FOR SAME, AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME AS ACTIVE INGREDIENT FOR PREVENTING OR TREATING VIRAL DISEASES
  申请人：Jung Young Sik

  公开号：US20140114068A1

  公开（公告）日：2014-04-24

  Disclosed are novel indanone derivatives, pharmaceutically acceptable salts thereof or enantiomers, a preparation method thereof, and a pharmaceutical composition for the prevention or treatment of viral diseases, comprising the same as an active ingredient. The indanone derivatives have excellent inhibitory activity against picornaviruses including coxsackie-, entero-, echo-, Polio-, and rhinoviruses, as well as exhibiting low cytotoxicity, so that they can be useful as an active ingredient of a pharmaceutical composition for the prevention or treatment of viral diseases including poliomyelitis, paralysis, acute hemorrhagic conjunctivitis, viral meningitis, hand-foot-and-mouth disease, vesicular disease, hepatitis A, myositis, myocarditis, pancreatitis, diabetes, epidemic myalgia, encephalitis, flu, herpangina, foot-and-mouth disease, asthma, chronic obstructive pulmonary disease, pneumonia, sinusitis or otitis media.

  揭示了新颖的茚酮衍生物，其药用盐或对映体，以及其制备方法和作为活性成分的用于预防或治疗病毒性疾病的药物组合物。这些茚酮衍生物对包括柯萨奇病毒、肠道病毒、回声病毒、脊髓灰质炎病毒和鼻病毒在内的小RNA病毒具有出色的抑制活性，并且具有低细胞毒性，因此它们可用作预防或治疗包括小儿麻痹症、瘫痪、急性出血性结膜炎、病毒性脑膜炎、手足口病、水疱病、甲型肝炎、肌炎、心肌炎、胰腺炎、糖尿病、流行性肌痛、脑炎、流感、手足口病、哮喘、慢性阻塞性肺病、肺炎、鼻窦炎或中耳炎等病毒性疾病的药物组合物的活性成分。
• US9464067B2
  申请人：——

  公开号：US9464067B2

  公开（公告）日：2016-10-11
• US9890133B2
  申请人：——

  公开号：US9890133B2

  公开（公告）日：2018-02-13
• 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.