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Synthesis and antiproliferative activity of pterostilbene and [Formula: see text]-methoxy pterostilbene Mannich base derivatives against Hela cells.

Liu C, Dong L, Wang S, Wang Q - Mol. Divers. (2015)

Bottom Line: Fourteen novel pterostilbene (1) and [Formula: see text]-methoxy pterostilbene (2) Mannich base derivatives (3-16) were synthesized via the microwave-assisted Mannich reaction of 1 or 2 with various secondary amines and formaldehyde.The regioselectivity of the reaction occurred preferentially at [Formula: see text] position of the B-ring of stilbene.Compounds 1-3, 7, 11-13, and 16 displayed higher (lower [Formula: see text] values) activity than the positive control cisplatin [Formula: see text].

View Article: PubMed Central - PubMed

Affiliation: College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082, People's Republic of China.

ABSTRACT
Fourteen novel pterostilbene (1) and [Formula: see text]-methoxy pterostilbene (2) Mannich base derivatives (3-16) were synthesized via the microwave-assisted Mannich reaction of 1 or 2 with various secondary amines and formaldehyde. The regioselectivity of the reaction occurred preferentially at [Formula: see text] position of the B-ring of stilbene. The biological testing results showed that all the target compounds exhibit antiproliferative activity against Hela cells from [Formula: see text]-[Formula: see text]. Compounds 1-3, 7, 11-13, and 16 displayed higher (lower [Formula: see text] values) activity than the positive control cisplatin [Formula: see text].

No MeSH data available.


Synthesis of pterostilbene and -methoxy pterostilbene Mannich base derivatives (3–16)
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Sch1: Synthesis of pterostilbene and -methoxy pterostilbene Mannich base derivatives (3–16)

Mentions: The synthetic route used for the construction of novel pterostilbene and -methoxy pterostilbene Mannich base derivatives (3–16) is shown in Scheme 1. Pterostilbene (1) and -methoxy pterostilbene (2) were synthesized by O-methylation, reduction, chlorination, Arbuzov rearrangement, and Wittig reaction using commercially available 3,5-dihydroxybenzoic acid, 4-hydroxybenzaldehyde, or vanillin as starting material as described previously by our group [15].Scheme 1


Synthesis and antiproliferative activity of pterostilbene and [Formula: see text]-methoxy pterostilbene Mannich base derivatives against Hela cells.

Liu C, Dong L, Wang S, Wang Q - Mol. Divers. (2015)

Synthesis of pterostilbene and -methoxy pterostilbene Mannich base derivatives (3–16)
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4591201&req=5

Sch1: Synthesis of pterostilbene and -methoxy pterostilbene Mannich base derivatives (3–16)
Mentions: The synthetic route used for the construction of novel pterostilbene and -methoxy pterostilbene Mannich base derivatives (3–16) is shown in Scheme 1. Pterostilbene (1) and -methoxy pterostilbene (2) were synthesized by O-methylation, reduction, chlorination, Arbuzov rearrangement, and Wittig reaction using commercially available 3,5-dihydroxybenzoic acid, 4-hydroxybenzaldehyde, or vanillin as starting material as described previously by our group [15].Scheme 1

Bottom Line: Fourteen novel pterostilbene (1) and [Formula: see text]-methoxy pterostilbene (2) Mannich base derivatives (3-16) were synthesized via the microwave-assisted Mannich reaction of 1 or 2 with various secondary amines and formaldehyde.The regioselectivity of the reaction occurred preferentially at [Formula: see text] position of the B-ring of stilbene.Compounds 1-3, 7, 11-13, and 16 displayed higher (lower [Formula: see text] values) activity than the positive control cisplatin [Formula: see text].

View Article: PubMed Central - PubMed

Affiliation: College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082, People's Republic of China.

ABSTRACT
Fourteen novel pterostilbene (1) and [Formula: see text]-methoxy pterostilbene (2) Mannich base derivatives (3-16) were synthesized via the microwave-assisted Mannich reaction of 1 or 2 with various secondary amines and formaldehyde. The regioselectivity of the reaction occurred preferentially at [Formula: see text] position of the B-ring of stilbene. The biological testing results showed that all the target compounds exhibit antiproliferative activity against Hela cells from [Formula: see text]-[Formula: see text]. Compounds 1-3, 7, 11-13, and 16 displayed higher (lower [Formula: see text] values) activity than the positive control cisplatin [Formula: see text].

No MeSH data available.