Metal-free visible-light induced cyclization/substitution cascade reaction of alkyne-tethered cyclohexadienones and diselenides: access to 5-hydroxy-3-selenyl-4a,8a-dihydro-2 H -chromen-6(5 H )-ones
A simple and efficient Se-radical triggered cyclization/substitution cascade reaction of alkyne-tethered cyclohexadienones to afford 5-hydroxy-3-selenyl-4a,8a-dihydro-2 H -chromen-6(5 H )-ones has been developed. This transformation via the 3,5-diselenyl-4a,8a-dihydro-2 H -chromen-6(5 H )-one interm...
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| Published in | Green chemistry : an international journal and green chemistry resource : GC Vol. 21; no. 13; pp. 3547 - 3551 |
|---|---|
| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
01.07.2019
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| Online Access | Get full text |
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| Abstract | A simple and efficient Se-radical triggered cyclization/substitution cascade reaction of alkyne-tethered cyclohexadienones to afford 5-hydroxy-3-selenyl-4a,8a-dihydro-2
H
-chromen-6(5
H
)-ones has been developed. This transformation
via
the 3,5-diselenyl-4a,8a-dihydro-2
H
-chromen-6(5
H
)-one intermediate followed by hydrolysis in the presence of CsOAc affords the desired product
3
. The resulting products were tested for their
in vitro
anticancer activity using MTT assay, and compounds
3e
and
3q
showed potent cancer cell-growth inhibition activities. |
|---|---|
| AbstractList | A simple and efficient Se-radical triggered cyclization/substitution cascade reaction of alkyne-tethered cyclohexadienones to afford 5-hydroxy-3-selenyl-4a,8a-dihydro-2
H
-chromen-6(5
H
)-ones has been developed. This transformation
via
the 3,5-diselenyl-4a,8a-dihydro-2
H
-chromen-6(5
H
)-one intermediate followed by hydrolysis in the presence of CsOAc affords the desired product
3
. The resulting products were tested for their
in vitro
anticancer activity using MTT assay, and compounds
3e
and
3q
showed potent cancer cell-growth inhibition activities. |
| Author | Feng, Xi-Yuan Chen, Yan-Yan Pan, Ying-Ming Ma, Xian-Li Mo, Zu-Yu Wang, Qian Xin, Mao Xu, Yan-Li |
| Author_xml | – sequence: 1 givenname: Xian-Li surname: Ma fullname: Ma, Xian-Li organization: Pharmacy School of Guilin Medical University, Guilin, 541004 People's Republic of China – sequence: 2 givenname: Qian surname: Wang fullname: Wang, Qian organization: Pharmacy School of Guilin Medical University, Guilin, 541004 People's Republic of China – sequence: 3 givenname: Xi-Yuan surname: Feng fullname: Feng, Xi-Yuan organization: State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences of Guangxi Normal University, Guilin 541004, People's Republic of China – sequence: 4 givenname: Zu-Yu surname: Mo fullname: Mo, Zu-Yu organization: State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences of Guangxi Normal University, Guilin 541004, People's Republic of China – sequence: 5 givenname: Ying-Ming orcidid: 0000-0002-3625-7647 surname: Pan fullname: Pan, Ying-Ming organization: State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences of Guangxi Normal University, Guilin 541004, People's Republic of China – sequence: 6 givenname: Yan-Yan surname: Chen fullname: Chen, Yan-Yan organization: Pharmacy School of Guilin Medical University, Guilin, 541004 People's Republic of China – sequence: 7 givenname: Mao surname: Xin fullname: Xin, Mao organization: Pharmacy School of Guilin Medical University, Guilin, 541004 People's Republic of China – sequence: 8 givenname: Yan-Li orcidid: 0000-0003-1373-6431 surname: Xu fullname: Xu, Yan-Li organization: Pharmacy School of Guilin Medical University, Guilin, 541004 People's Republic of China |
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