Research output: Contribution to journal › Article › peer-review
New crystal forms for biologically active compounds. Part 2 : Anastrozole as n-substituted 1,2,4-triazole in halogen bonding and lp-π interactions with 1,4-diiodotetrafluorobenzene. / Kryukova, Mariya A.; Sapegin, Alexander V.; Novikov, Alexander S.; Krasavin, Mikhail; Ivanov, Daniil M.
In: Crystals, Vol. 10, No. 5, 371, 05.2020.Research output: Contribution to journal › Article › peer-review
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TY - JOUR
T1 - New crystal forms for biologically active compounds. Part 2
T2 - Anastrozole as n-substituted 1,2,4-triazole in halogen bonding and lp-π interactions with 1,4-diiodotetrafluorobenzene
AU - Kryukova, Mariya A.
AU - Sapegin, Alexander V.
AU - Novikov, Alexander S.
AU - Krasavin, Mikhail
AU - Ivanov, Daniil M.
PY - 2020/5
Y1 - 2020/5
N2 - For an active pharmaceutical ingredient, it is important to stabilize its specific crystal polymorph. If the potential interconversion of various polymorphs is not carefully controlled, it may lead to deterioration of the drug’s physicochemical profile and, ultimately, its therapeutic efficacy. The desired polymorph stabilization can be achieved via co-crystallization with appropriate crystallophoric excipients. In this work, we identified an opportunity for co-crystallization of anastrozole (ASZ), a well-known aromatase inhibitor useful in second-line therapy of estrogen-dependent breast cancer, with a classical XB donor, 1,2,4,5-tetrafluoro-3,6-diiodobenzene (1,4-FIB). In the X-ray structures of ASZ·1.5 (1,4-FIB) co-crystal, different non-covalent interactions involving hydrogen and halogen atoms were detected and studied by quantum chemical calculations and QTAIM analysis at the ωB97XD/DZP-DKH level of theory.
AB - For an active pharmaceutical ingredient, it is important to stabilize its specific crystal polymorph. If the potential interconversion of various polymorphs is not carefully controlled, it may lead to deterioration of the drug’s physicochemical profile and, ultimately, its therapeutic efficacy. The desired polymorph stabilization can be achieved via co-crystallization with appropriate crystallophoric excipients. In this work, we identified an opportunity for co-crystallization of anastrozole (ASZ), a well-known aromatase inhibitor useful in second-line therapy of estrogen-dependent breast cancer, with a classical XB donor, 1,2,4,5-tetrafluoro-3,6-diiodobenzene (1,4-FIB). In the X-ray structures of ASZ·1.5 (1,4-FIB) co-crystal, different non-covalent interactions involving hydrogen and halogen atoms were detected and studied by quantum chemical calculations and QTAIM analysis at the ωB97XD/DZP-DKH level of theory.
KW - Anastrozole
KW - DFT
KW - Halogen bonding
KW - Lp-π interactions
KW - Non-covalent interactions
KW - QTAIM
KW - non-covalent interactions
KW - HYDROGEN-BOND
KW - CENTER-DOT-N
KW - COMPLEXES
KW - REACTIVITY
KW - NONCOVALENT INTERACTIONS
KW - SOLID-STATE
KW - DENSITY
KW - ENERGETIC PROPERTIES
KW - lp-pi interactions
KW - anastrozole
KW - COORDINATION POLYMERS
KW - halogen bonding
KW - ZETA BASIS-SETS
UR - http://www.scopus.com/inward/record.url?scp=85084363772&partnerID=8YFLogxK
UR - https://www.mendeley.com/catalogue/89f31580-6382-3548-afa7-5f64f3ccebc4/
U2 - 10.3390/cryst10050371
DO - 10.3390/cryst10050371
M3 - Article
AN - SCOPUS:85084363772
VL - 10
JO - Liquid Crystals Today
JF - Liquid Crystals Today
SN - 1358-314X
IS - 5
M1 - 371
ER -
ID: 53530543