Synthesis and anti-influenza virus activity evaluation of novel andrographolide derivatives

In this paper, using AI78-38 , an andrographolide analog with novel skeleton, as the lead compound, we designed and synthesized fifteen amide derivatives at the 17 position of AI78-38 . In the synthesis of key intermediate IM4 , the low yield of the SeO 2 oxidation step impeded the further study. Ai...

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Published in	Medicinal chemistry research Vol. 31; no. 11; pp. 1959 - 1973
Main Authors	Zou, Chunyang, Men, Jinyu, Qu, Yingjin, Jiang, Chunfeng, Wang, Yao, Chen, Lixia, Yuan, Lei
Format	Journal Article
Language	English
Published	New York Springer US 01.11.2022 Springer Nature B.V
Subjects	Bioavailability Biochemistry Biomedical and Life Sciences Biomedicine Bioorganic Chemistry Influenza Influenza A Inorganic Chemistry Lead compounds Medicinal Chemistry Original Research Oxidation Pharmacology/Toxicology Reagents Ribavirin Selenium dioxide Substrates Synthesis Viruses White reagent catalysis Anti-influenza A virus activity Cyclic substrate Andrographolide Double bond migration
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Abstract	In this paper, using AI78-38 , an andrographolide analog with novel skeleton, as the lead compound, we designed and synthesized fifteen amide derivatives at the 17 position of AI78-38 . In the synthesis of key intermediate IM4 , the low yield of the SeO 2 oxidation step impeded the further study. Aiming at improving the yield, White reagent was applied to furnish IM4 by catalyzing the allylic C–H oxidation at the 7, 8, 17 position. It is also firstly reported that White reagent possessed the ability of oxidating the cyclic substrates. Compared with SeO 2 oxidative approach, the modified synthetic method utilized by White reagent increased the yield from 32.0 to 53.6%. The anti-influenza A virus (H3N2) results showed that 4-methoxy derivative 10 offered the greatest inhibitory ability, with an IC 50 value of 90.2 μg/ml, slightly more potent than ribavirin. Furthermore, the drug-likeness and ADMET properties of compound 10 and AI78-38 were evaluated using the Discovery Studio 2.1 software and the online SwissADME. The results showed that compound 10 offered good bioavailability and overcame the disadvantages of the ADMET properties in AI78-38 . Graphical abstract
AbstractList	In this paper, using AI78-38 , an andrographolide analog with novel skeleton, as the lead compound, we designed and synthesized fifteen amide derivatives at the 17 position of AI78-38 . In the synthesis of key intermediate IM4 , the low yield of the SeO 2 oxidation step impeded the further study. Aiming at improving the yield, White reagent was applied to furnish IM4 by catalyzing the allylic C–H oxidation at the 7, 8, 17 position. It is also firstly reported that White reagent possessed the ability of oxidating the cyclic substrates. Compared with SeO 2 oxidative approach, the modified synthetic method utilized by White reagent increased the yield from 32.0 to 53.6%. The anti-influenza A virus (H3N2) results showed that 4-methoxy derivative 10 offered the greatest inhibitory ability, with an IC 50 value of 90.2 μg/ml, slightly more potent than ribavirin. Furthermore, the drug-likeness and ADMET properties of compound 10 and AI78-38 were evaluated using the Discovery Studio 2.1 software and the online SwissADME. The results showed that compound 10 offered good bioavailability and overcame the disadvantages of the ADMET properties in AI78-38 . Graphical abstract In this paper, using AI78-38, an andrographolide analog with novel skeleton, as the lead compound, we designed and synthesized fifteen amide derivatives at the 17 position of AI78-38. In the synthesis of key intermediate IM4, the low yield of the SeO2 oxidation step impeded the further study. Aiming at improving the yield, White reagent was applied to furnish IM4 by catalyzing the allylic C–H oxidation at the 7, 8, 17 position. It is also firstly reported that White reagent possessed the ability of oxidating the cyclic substrates. Compared with SeO2 oxidative approach, the modified synthetic method utilized by White reagent increased the yield from 32.0 to 53.6%. The anti-influenza A virus (H3N2) results showed that 4-methoxy derivative 10 offered the greatest inhibitory ability, with an IC50 value of 90.2 μg/ml, slightly more potent than ribavirin. Furthermore, the drug-likeness and ADMET properties of compound 10 and AI78-38 were evaluated using the Discovery Studio 2.1 software and the online SwissADME. The results showed that compound 10 offered good bioavailability and overcame the disadvantages of the ADMET properties in AI78-38.
Author	Wang, Yao Yuan, Lei Qu, Yingjin Men, Jinyu Zou, Chunyang Jiang, Chunfeng Chen, Lixia
Author_xml	– sequence: 1 givenname: Chunyang surname: Zou fullname: Zou, Chunyang email: zcy19980619@163.com organization: Department of Pharmacy, Liaoning Vocational College of Medicine, Liaoning Institute of Basic Medicine – sequence: 2 givenname: Jinyu surname: Men fullname: Men, Jinyu organization: Shenyang Pharmaceutical University – sequence: 3 givenname: Yingjin surname: Qu fullname: Qu, Yingjin organization: Shenyang Pharmaceutical University – sequence: 4 givenname: Chunfeng surname: Jiang fullname: Jiang, Chunfeng organization: Liaoning Institute of Science and Technology – sequence: 5 givenname: Yao surname: Wang fullname: Wang, Yao organization: Department of Pharmacy, Liaoning Vocational College of Medicine, Liaoning Institute of Basic Medicine – sequence: 6 givenname: Lixia surname: Chen fullname: Chen, Lixia organization: Shenyang Pharmaceutical University – sequence: 7 givenname: Lei surname: Yuan fullname: Yuan, Lei email: leiyuan@syphu.edu.cn organization: Shenyang Pharmaceutical University
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Snippet	In this paper, using AI78-38 , an andrographolide analog with novel skeleton, as the lead compound, we designed and synthesized fifteen amide derivatives at... In this paper, using AI78-38, an andrographolide analog with novel skeleton, as the lead compound, we designed and synthesized fifteen amide derivatives at the...
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StartPage	1959
SubjectTerms	Bioavailability Biochemistry Biomedical and Life Sciences Biomedicine Bioorganic Chemistry Influenza Influenza A Inorganic Chemistry Lead compounds Medicinal Chemistry Original Research Oxidation Pharmacology/Toxicology Reagents Ribavirin Selenium dioxide Substrates Synthesis Viruses
Title	Synthesis and anti-influenza virus activity evaluation of novel andrographolide derivatives
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