Synthesis of carbocyclic analogs of dehydroaltenusin:
identification of a stable inhibitor of calf DNA polymerase a

J 2015

Synthesis of carbocyclic analogs of dehydroaltenusin: identification of a stable inhibitor of calf DNA polymerase a

KOVÁČOVÁ, Silvia, Santosh Kumar ADLA, Lukáš MAIER, Michal BABIAK, Yoshiyuki MIZUSHINA et. al.

Základní údaje

Originální název

Synthesis of carbocyclic analogs of dehydroaltenusin: identification of a stable inhibitor of calf DNA polymerase a

Autoři

KOVÁČOVÁ, Silvia (703 Slovensko, domácí), Santosh Kumar ADLA (356 Indie, domácí), Lukáš MAIER (203 Česká republika, domácí), Michal BABIAK (703 Slovensko, domácí), Yoshiyuki MIZUSHINA (392 Japonsko) a Kamil PARUCH (203 Česká republika, domácí)

Vydání

Tetrahedron, Pergamon Press, 2015, 0040-4020

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Velká Británie a Severní Irsko

Utajení

není předmětem státního či obchodního tajemství

Impakt faktor

Impact factor: 2.645

Kód RIV

RIV/00216224:14310/15:00083970

Organizační jednotka

Přírodovědecká fakulta

DOI

http://dx.doi.org/10.1016/j.tet.2015.08.005

UT WoS

000361161500007

Klíčová slova anglicky

Dehydroaltenusin; DNA polymerase; DNA damage repair; Spirocyclic compounds; Regioselective aldol condensation

Štítky

AKR, rivok

Změněno: 12. 4. 2016 14:03, Ing. Andrea Mikešková

Anotace

V originále

Syntheses of carbocyclic analogs of dehydroaltenusin tautomers are reported. Both target compounds, cDHA (2,8-dihydroxy-6-methoxy-10a-methyl-10,10a-dihydrophenanthrene-3,9-dione) and cDHAs (4,5-dihydroxy-6-methoxy-2-methylspiro[cyclohexa[2,5]diene-1,1-indene]-3,4(2H)-dione), were prepared from 3,5-dimethoxybenzaldehyde in 11 and 13 steps, respectively. Unlike dehydroaltenusin, both cDHA and cDHAs are stable and their structures were confirmed by X-ray crystallography. Compound cDHA was found to be active against calf DNA polymerase a but not related isozymes, while the spirocyclic analog cDHAs was inactive.

Citovat

KOVÁČOVÁ, Silvia, Santosh Kumar ADLA, Lukáš MAIER, Michal BABIAK, Yoshiyuki MIZUSHINA a Kamil PARUCH. Synthesis of carbocyclic analogs of dehydroaltenusin: identification of a stable inhibitor of calf DNA polymerase a. Tetrahedron. Pergamon Press, 2015, roč. 71, č. 40, s. 7575-7582. ISSN 0040-4020. Dostupné z: https://dx.doi.org/10.1016/j.tet.2015.08.005.

@article{1312067,
   author = {Kováčová, Silvia and Adla, Santosh Kumar and Maier, Lukáš and Babiak, Michal and Mizushina, Yoshiyuki and Paruch, Kamil},
   article_number = {40},
   doi = {http://dx.doi.org/10.1016/j.tet.2015.08.005},
   keywords = {Dehydroaltenusin; DNA polymerase; DNA damage repair; Spirocyclic compounds; Regioselective aldol condensation},
   language = {eng},
   issn = {0040-4020},
   journal = {Tetrahedron},
   title = {Synthesis of carbocyclic analogs of dehydroaltenusin: identification of a stable inhibitor of calf DNA polymerase a},
   volume = {71},
   year = {2015}
}

TY  - JOUR
ID  - 1312067
AU  - Kováčová, Silvia - Adla, Santosh Kumar - Maier, Lukáš - Babiak, Michal - Mizushina, Yoshiyuki - Paruch, Kamil
PY  - 2015
TI  - Synthesis of carbocyclic analogs of dehydroaltenusin: identification of a stable inhibitor of calf DNA polymerase a
JF  - Tetrahedron
VL  - 71
IS  - 40
SP  - 7575-7582
EP  - 7575-7582
PB  - Pergamon Press
SN  - 00404020
KW  - Dehydroaltenusin
KW  - DNA polymerase
KW  - DNA damage repair
KW  - Spirocyclic compounds
KW  - Regioselective aldol condensation
N2  - Syntheses of carbocyclic analogs of dehydroaltenusin tautomers are reported. Both target compounds, cDHA (2,8-dihydroxy-6-methoxy-10a-methyl-10,10a-dihydrophenanthrene-3,9-dione) and cDHAs (4,5-dihydroxy-6-methoxy-2-methylspiro[cyclohexa[2,5]diene-1,1-indene]-3,4(2H)-dione), were prepared from 3,5-dimethoxybenzaldehyde in 11 and 13 steps, respectively. Unlike dehydroaltenusin, both cDHA and cDHAs are stable and their structures were confirmed by X-ray crystallography. Compound cDHA was found to be active against calf DNA polymerase a but not related isozymes, while the spirocyclic analog cDHAs was inactive.
ER  -

KOVÁČOVÁ, Silvia, Santosh Kumar ADLA, Lukáš MAIER, Michal BABIAK, Yoshiyuki MIZUSHINA a Kamil PARUCH. Synthesis of carbocyclic analogs of dehydroaltenusin: identification of a stable inhibitor of calf DNA polymerase a. \textit{Tetrahedron}. Pergamon Press, 2015, roč.~71, č.~40, s.~7575-7582. ISSN~0040-4020. Dostupné z: https://dx.doi.org/10.1016/j.tet.2015.08.005.

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