Structural characteristics of thiosemicarbazones as inhibitors of melanogenesis

Ki Cheul Lee; Pillaiyar Thanigaimalai; Vinay K. Sharma; Min Seok Kim; Eunmiri Roh; Bang Yeon Hwang; Youngsoo Kim; Sang Hun Jung

doi:10.1016/j.bmcl.2010.08.114

Structural characteristics of thiosemicarbazones as inhibitors of melanogenesis

Ki Cheul Lee, Pillaiyar Thanigaimalai, Vinay K. Sharma, Min Seok Kim, Eunmiri Roh, Bang Yeon Hwang, Youngsoo Kim, Sang Hun Jung

Hormel Institute

Research output: Contribution to journal › Article › peer-review

34 Scopus citations

Abstract

A series of thiosemicarbazones 2(e-s) have been synthesized and studied their structure-activity relationship as melanogenesis inhibitor. Among them, (Z)-2-(naphthalen-1-ylmethylene)hydrazinecarbothioamide (2q, >100% inhibition at 10 μM, IC₅₀ = 1.1 μM, C log P = 3.039) showed the strongest inhibitory activity. Regarding their structure-activity relationship, the hydrophobic substituents regardless the position on phenyl ring of benzaldehyde thiosemicarbazones enhance the inhibitory activity. Furthermore, the aromatic group of benzaldehydethiosemicarbazones can be replaced with sterically bulky cyclohexyl. Thus, hydrophobicity of the aryl or alkyl group on hydrazine of thiosemicarbazones is determinant factor for their inhibitory activity in melanogenesis rather than planarity.

Original language	English (US)
Pages (from-to)	6794-6796
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	20
Issue number	22
DOIs	https://doi.org/10.1016/j.bmcl.2010.08.114
State	Published - Nov 15 2010

Bibliographical note

Funding Information:
This work was supported by a grant ( R01-2007-000-20099-0 ) and Priority Research Centers Program ( 2009-0093815 ) through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology.

Keywords

Hydrophobicity
Melanogenesis inhibitor
Thiosemicarbazones

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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title = "Structural characteristics of thiosemicarbazones as inhibitors of melanogenesis",

abstract = "A series of thiosemicarbazones 2(e-s) have been synthesized and studied their structure-activity relationship as melanogenesis inhibitor. Among them, (Z)-2-(naphthalen-1-ylmethylene)hydrazinecarbothioamide (2q, >100% inhibition at 10 μM, IC50 = 1.1 μM, C log P = 3.039) showed the strongest inhibitory activity. Regarding their structure-activity relationship, the hydrophobic substituents regardless the position on phenyl ring of benzaldehyde thiosemicarbazones enhance the inhibitory activity. Furthermore, the aromatic group of benzaldehydethiosemicarbazones can be replaced with sterically bulky cyclohexyl. Thus, hydrophobicity of the aryl or alkyl group on hydrazine of thiosemicarbazones is determinant factor for their inhibitory activity in melanogenesis rather than planarity.",

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AU - Roh, Eunmiri

AU - Hwang, Bang Yeon

AU - Kim, Youngsoo

AU - Jung, Sang Hun

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Structural characteristics of thiosemicarbazones as inhibitors of melanogenesis

Abstract

Bibliographical note

Keywords

UN SDGs

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