Structure-activity relationship of naphthaldehydethiosemicarbazones in melanogenesis inhibition

Pillaiyar Thanigaimalai; Eeda Venkateswara Rao; Ki Cheul Lee; Vinay K. Sharma; Eunmiri Roh; Youngsoo Kim; Sang Hun Jung

doi:10.1016/j.bmcl.2011.12.035

Structure-activity relationship of naphthaldehydethiosemicarbazones in melanogenesis inhibition

Pillaiyar Thanigaimalai, Eeda Venkateswara Rao, Ki Cheul Lee, Vinay K. Sharma, Eunmiri Roh, Youngsoo Kim, Sang Hun Jung

The Hormel Institute

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

16 Scopus citations

Abstract

2-(Naphthalen-1-ylmethylene)hydrazinecarbothioamide (14, IC ₅₀ = 1.1 μM) was discovered as a highly potent inhibitor of melanogenesis. To define the role of hydrogens (at N1 and N3) and sulfur in 14, a series of analogs 15a-p were synthesized and evaluated for anti-melanogenic activity using melanoma B16 cells under the stimulus of α-MSH. It was observed that replacement of either of these hydrogens at N1 or N3 by substituents increases the activity significantly. Conversely, concomitant substitutions decrease the inhibitory potency. In addition, the presence of sulfur in thiosemicarbazone is essential for the activity.

Original language	English (US)
Pages (from-to)	886-889
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	22
Issue number	2
DOIs	https://doi.org/10.1016/j.bmcl.2011.12.035
State	Published - Jan 15 2012

Bibliographical note

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

Keywords

2-(Naphthalen-1-ylmethylene) hydrazinecarbothioamide
Melanogenesis inhibitor
Skin whitening agent
Thiosemicarbazone

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10.1016/j.bmcl.2011.12.035

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abstract = "2-(Naphthalen-1-ylmethylene)hydrazinecarbothioamide (14, IC 50 = 1.1 μM) was discovered as a highly potent inhibitor of melanogenesis. To define the role of hydrogens (at N1 and N3) and sulfur in 14, a series of analogs 15a-p were synthesized and evaluated for anti-melanogenic activity using melanoma B16 cells under the stimulus of α-MSH. It was observed that replacement of either of these hydrogens at N1 or N3 by substituents increases the activity significantly. Conversely, concomitant substitutions decrease the inhibitory potency. In addition, the presence of sulfur in thiosemicarbazone is essential for the activity.",

keywords = "2-(Naphthalen-1-ylmethylene) hydrazinecarbothioamide, Melanogenesis inhibitor, Skin whitening agent, Thiosemicarbazone",

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AU - Thanigaimalai, Pillaiyar

AU - Rao, Eeda Venkateswara

AU - Lee, Ki Cheul

AU - Sharma, Vinay K.

AU - Roh, Eunmiri

AU - Kim, Youngsoo

AU - Jung, Sang Hun

N1 - Funding Information: This work was supported by a Priority Research Centers Program (2009-0093815) through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology .

PY - 2012/1/15

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N2 - 2-(Naphthalen-1-ylmethylene)hydrazinecarbothioamide (14, IC 50 = 1.1 μM) was discovered as a highly potent inhibitor of melanogenesis. To define the role of hydrogens (at N1 and N3) and sulfur in 14, a series of analogs 15a-p were synthesized and evaluated for anti-melanogenic activity using melanoma B16 cells under the stimulus of α-MSH. It was observed that replacement of either of these hydrogens at N1 or N3 by substituents increases the activity significantly. Conversely, concomitant substitutions decrease the inhibitory potency. In addition, the presence of sulfur in thiosemicarbazone is essential for the activity.

AB - 2-(Naphthalen-1-ylmethylene)hydrazinecarbothioamide (14, IC 50 = 1.1 μM) was discovered as a highly potent inhibitor of melanogenesis. To define the role of hydrogens (at N1 and N3) and sulfur in 14, a series of analogs 15a-p were synthesized and evaluated for anti-melanogenic activity using melanoma B16 cells under the stimulus of α-MSH. It was observed that replacement of either of these hydrogens at N1 or N3 by substituents increases the activity significantly. Conversely, concomitant substitutions decrease the inhibitory potency. In addition, the presence of sulfur in thiosemicarbazone is essential for the activity.

KW - 2-(Naphthalen-1-ylmethylene) hydrazinecarbothioamide

KW - Melanogenesis inhibitor

KW - Skin whitening agent

KW - Thiosemicarbazone

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Structure-activity relationship of naphthaldehydethiosemicarbazones in melanogenesis inhibition

Abstract

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Keywords

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