Structural requirement(s) of N-phenylthioureas and benzaldehyde thiosemicarbazones as inhibitors of melanogenesis in melanoma B 16 cells

P. Thanigaimalai; Tuan Anh Le Hoang; Ki Cheul Lee; Seong Cheol Bang; Vinay K. Sharma; Cheong Yong Yun; Eunmiri Roh; Bang Yeon Hwang; Youngsoo Kim; Sang Hun Jung

doi:10.1016/j.bmcl.2010.02.067

Structural requirement(s) of N-phenylthioureas and benzaldehyde thiosemicarbazones as inhibitors of melanogenesis in melanoma B 16 cells

P. Thanigaimalai
, Tuan Anh Le Hoang
, Ki Cheul Lee
, Seong Cheol Bang
, Vinay K. Sharma
, Cheong Yong Yun
, Eunmiri Roh
, Bang Yeon Hwang
, Youngsoo Kim
, Sang Hun Jung

The Hormel Institute

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

64 Scopus citations

Abstract

In order to define the structural requirements of phenylthiourea (PTU), a series of thiourea and thiosemicarbazone analogs were prepared and evaluated as inhibitors of melanogenesis in melanoma B16 cells. The most potent analog was 2-(4-tert-butylbenzylidene)hydrazinecarbothioamide (1u) with an IC₅₀ value of 2.7 μM in inhibition of melanogenesis. The structure for potent inhibitory activity of these derivatives are required with the direct connection of π-planar structure to thiourea without steric hinderance in PTU derivatives and the hydrophobic substituent at para position in case of semicarbazones.

Original language	English (US)
Pages (from-to)	2991-2993
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	20
Issue number	9
DOIs	https://doi.org/10.1016/j.bmcl.2010.02.067
State	Published - May 1 2010

Bibliographical note

Funding Information:
This research was financially supported by a grant ( R01-2007-000-20099-0 ) from the National Research Foundation of Korea

Copyright:
Copyright 2010 Elsevier B.V., All rights reserved.

UN SDGs

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

SDG 3 Good Health and Well-being

Keywords

Melanogenesis inhibitor
Phenylthiourea and benzaldehyde thiosemicarbazone
Tyrosinase inhibitor

Publisher link

10.1016/j.bmcl.2010.02.067

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Thanigaimalai, P., Le Hoang, T. A., Lee, K. C., Bang, S. C., Sharma, V. K., Yun, C. Y., Roh, E., Hwang, B. Y., Kim, Y., & Jung, S. H. (2010). Structural requirement(s) of N-phenylthioureas and benzaldehyde thiosemicarbazones as inhibitors of melanogenesis in melanoma B 16 cells. Bioorganic and Medicinal Chemistry Letters, 20(9), 2991-2993. https://doi.org/10.1016/j.bmcl.2010.02.067

Thanigaimalai, P, Le Hoang, TA, Lee, KC, Bang, SC, Sharma, VK, Yun, CY, Roh, E, Hwang, BY, Kim, Y & Jung, SH 2010, 'Structural requirement(s) of N-phenylthioureas and benzaldehyde thiosemicarbazones as inhibitors of melanogenesis in melanoma B 16 cells', Bioorganic and Medicinal Chemistry Letters, vol. 20, no. 9, pp. 2991-2993. https://doi.org/10.1016/j.bmcl.2010.02.067

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abstract = "In order to define the structural requirements of phenylthiourea (PTU), a series of thiourea and thiosemicarbazone analogs were prepared and evaluated as inhibitors of melanogenesis in melanoma B16 cells. The most potent analog was 2-(4-tert-butylbenzylidene)hydrazinecarbothioamide (1u) with an IC50 value of 2.7 μM in inhibition of melanogenesis. The structure for potent inhibitory activity of these derivatives are required with the direct connection of π-planar structure to thiourea without steric hinderance in PTU derivatives and the hydrophobic substituent at para position in case of semicarbazones.",

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AU - Lee, Ki Cheul

AU - Bang, Seong Cheol

AU - Sharma, Vinay K.

AU - Yun, Cheong Yong

AU - Roh, Eunmiri

AU - Hwang, Bang Yeon

AU - Kim, Youngsoo

AU - Jung, Sang Hun

N1 - Funding Information: This research was financially supported by a grant ( R01-2007-000-20099-0 ) from the National Research Foundation of Korea Copyright: Copyright 2010 Elsevier B.V., All rights reserved.

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N2 - In order to define the structural requirements of phenylthiourea (PTU), a series of thiourea and thiosemicarbazone analogs were prepared and evaluated as inhibitors of melanogenesis in melanoma B16 cells. The most potent analog was 2-(4-tert-butylbenzylidene)hydrazinecarbothioamide (1u) with an IC50 value of 2.7 μM in inhibition of melanogenesis. The structure for potent inhibitory activity of these derivatives are required with the direct connection of π-planar structure to thiourea without steric hinderance in PTU derivatives and the hydrophobic substituent at para position in case of semicarbazones.

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KW - Melanogenesis inhibitor

KW - Phenylthiourea and benzaldehyde thiosemicarbazone

KW - Tyrosinase inhibitor

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Structural requirement(s) of N-phenylthioureas and benzaldehyde thiosemicarbazones as inhibitors of melanogenesis in melanoma B 16 cells

Abstract

Bibliographical note

UN SDGs

Keywords

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