Title:
SULFUR-CONTAINING ARTEMISININ ANALOGUE DIMER, AND PREPARATION METHOD THEREFOR AND USE THEREOF
Document Type and Number:
WIPO Patent Application WO/2023/240920
Kind Code:
A1
Abstract:
The present invention relates to a sulfur-containing artemisinin analogue dimer, and a preparation method therefor and the use thereof, which belong to the technical field of pharmaceutical chemistry. The sulfur-containing artemisinin analogue dimer is a compound having a chemical structural formula represented by formula I or a pharmaceutically acceptable salt thereof, wherein W represents any one of S, SO and SO2; Z represents any one of S, SO, SO2, O, NR1 and CR1
2; Y represents any one of a single bond, an alkyl group, an aryl group, a cyclic group, ether and ammonia; R1 represents any one of hydrogen, halogen, an alkyl group, an aryl group, a cyclic group, ether and ammonia; and n and m are each independently selected from integers of 0-15. Further disclosed in the present invention is a method for preparing a sulfur-containing artemisinin analogue dimer. The sulfur-containing artemisinin analogue dimer of the present invention has a selective inhibition effect on the growth of human cancer cell strains.
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Inventors:
LI JIANFENG (CN)
WANG XIAOTING (CN)
BA DEWEI (CN)
ZHOU QIXIN (CN)
KONG DI (CN)
HUANG CHENZHOU (CN)
WANG ZHENGXUE (CN)
YU KAIBO (CN)
XIONG WEI (CN)
HU WENHUA (CN)
LI ZHIQIANG (CN)
WANG JINLONG (CN)
LI MINGFENG (CN)
WANG XIAOTING (CN)
BA DEWEI (CN)
ZHOU QIXIN (CN)
KONG DI (CN)
HUANG CHENZHOU (CN)
WANG ZHENGXUE (CN)
YU KAIBO (CN)
XIONG WEI (CN)
HU WENHUA (CN)
LI ZHIQIANG (CN)
WANG JINLONG (CN)
LI MINGFENG (CN)
Application Number:
PCT/CN2022/131906
Publication Date:
December 21, 2023
Filing Date:
November 15, 2022
Export Citation:
Assignee:
SHURELI BIOPHARMA CO LTD (CN)
International Classes:
C07D519/00; A61K31/357; A61P35/00; C07D493/18
Domestic Patent References:
| WO2013130725A1 | 2013-09-06 |
Foreign References:
| CN101421276A | 2009-04-29 | |||
| CN107383048A | 2017-11-24 |
Other References:
GAUR RASHMI, CHEEMA HARVEER SINGH, KUMAR YOGESH, SINGH SURIYA PRATAP, YADAV DHARMENDRA K., DAROKAR MAHENDRA PADURANG, KHAN FEROZ, : "In vitro antimalarial activity and molecular modeling studies of novel artemisinin derivatives", RSC ADVANCES, ROYAL SOCIETY OF CHEMISTRY, GB, vol. 5, no. 59, 1 January 2015 (2015-01-01), GB , pages 47959 - 47974, XP093117497, ISSN: 2046-2069, DOI: 10.1039/C5RA07697H
VENUGOPALAN, B. ET AL.: "Antimalarial Activity of New Ethers and Thioethers of Dihydroartemisinin", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol. 30, no. 9, 31 December 1995 (1995-12-31), XP004040197, DOI: 10.1016/0223-5234(96)88287-0
DATABASE Registry 8 June 2008 (2008-06-08), ANONYMOUS: "3,12-Epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin, 10-[[[4-[[[(3R,5aS,6R,8aS,9R,10S,12S,12aR)-decahydro-3,6,9-trimethyl-3,12- epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10- yl]thio]methyl]phenyl]methyl]thio]decahydro-3,6,9-trimethyl-, (3R,5aS,6R,8aS,9R,10S,12S,12aR)- (CA INDEX NAME)", XP093117502, retrieved from STNext Database accession no. 1026475-31-9
SHEN SHENGQIANG, CHEN WEI, DONG LILI, YANG QING, LU HUIZHE, ZHANG JIANJUN: "Design and synthesis of naphthalimide group-bearing thioglycosides as novel β- N -acetylhexosaminidases inhibitors", JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, INFORMA HEALTHCARE, GB, vol. 33, no. 1, 1 January 2018 (2018-01-01), GB , pages 445 - 452, XP093117498, ISSN: 1475-6366, DOI: 10.1080/14756366.2017.1419217
OH SANGTAE, JEONG IN HOWA, LEE SEOKJOON: "Efficient Synthesis of e xo -Olefinated Deoxoartemisinin Derivatives by Ramberg−Bäcklund Rearrangement", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 69, no. 3, 1 February 2004 (2004-02-01), pages 984 - 986, XP093117499, ISSN: 0022-3263, DOI: 10.1021/jo035505x
JACOBINE ALEXANDER M., MAZZONE JENNIFER R., SLACK RACHEL D., TRIPATHI ABHAI K., SULLIVAN DAVID J., POSNER GARY H.: "Malaria-Infected Mice Live Until at Least Day 30 after a New Artemisinin-Derived Thioacetal Thiocarbonate Combined with Mefloquine Are Administered Together in a Single, Low, Oral Dose", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 55, no. 17, 13 September 2012 (2012-09-13), US , pages 7892 - 7899, XP093117500, ISSN: 0022-2623, DOI: 10.1021/jm3009986
VENUGOPALAN, B. ET AL.: "Antimalarial Activity of New Ethers and Thioethers of Dihydroartemisinin", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol. 30, no. 9, 31 December 1995 (1995-12-31), XP004040197, DOI: 10.1016/0223-5234(96)88287-0
DATABASE Registry 8 June 2008 (2008-06-08), ANONYMOUS: "3,12-Epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin, 10-[[[4-[[[(3R,5aS,6R,8aS,9R,10S,12S,12aR)-decahydro-3,6,9-trimethyl-3,12- epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10- yl]thio]methyl]phenyl]methyl]thio]decahydro-3,6,9-trimethyl-, (3R,5aS,6R,8aS,9R,10S,12S,12aR)- (CA INDEX NAME)", XP093117502, retrieved from STNext Database accession no. 1026475-31-9
SHEN SHENGQIANG, CHEN WEI, DONG LILI, YANG QING, LU HUIZHE, ZHANG JIANJUN: "Design and synthesis of naphthalimide group-bearing thioglycosides as novel β- N -acetylhexosaminidases inhibitors", JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, INFORMA HEALTHCARE, GB, vol. 33, no. 1, 1 January 2018 (2018-01-01), GB , pages 445 - 452, XP093117498, ISSN: 1475-6366, DOI: 10.1080/14756366.2017.1419217
OH SANGTAE, JEONG IN HOWA, LEE SEOKJOON: "Efficient Synthesis of e xo -Olefinated Deoxoartemisinin Derivatives by Ramberg−Bäcklund Rearrangement", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 69, no. 3, 1 February 2004 (2004-02-01), pages 984 - 986, XP093117499, ISSN: 0022-3263, DOI: 10.1021/jo035505x
JACOBINE ALEXANDER M., MAZZONE JENNIFER R., SLACK RACHEL D., TRIPATHI ABHAI K., SULLIVAN DAVID J., POSNER GARY H.: "Malaria-Infected Mice Live Until at Least Day 30 after a New Artemisinin-Derived Thioacetal Thiocarbonate Combined with Mefloquine Are Administered Together in a Single, Low, Oral Dose", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 55, no. 17, 13 September 2012 (2012-09-13), US , pages 7892 - 7899, XP093117500, ISSN: 0022-2623, DOI: 10.1021/jm3009986
Attorney, Agent or Firm:
KEYCOM PARTNERS, P.C. (CN)
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