Ketonethiosemicarbazones: structure-activity relationships for their melanogenesis inhibition |
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Authors: | Thanigaimalai Pillaiyar Lee Ki-Cheul Sharma Vinay K Roh Eunmiri Kim Youngsoo Jung Sang-Hun |
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Institution: | a College of Pharmacy and Institute of Drug Research and Development, Chungnam National University, Daejeon 305-764, Republic of Korea b College of Pharmacy, Chungbuk National University, Cheongju 361-763, Republic of Korea |
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Abstract: | A series of 2-(1-phenylalkylidene)hydrazinecarbothioamides 2, 2-(1-phenylalkyl)hydrazinecarbothioamides 3, 2-(3,4-dihydronaphthalen-1(2H)-ylidene)hydrazinecarbothioamide (4), and 2-(1-(thiophen-2-yl)ethylidene)hydrazinecarbothioamide (5) were synthesized for their melanogenesis inhibition in melanoma B16 cells. The SAR of these ketonethiosemicarbazones revealed that the benzylidene hydrogen in aldehydethiosemicarbazones 1 can be replaced by hydrophobic moiety and substitutions with alkyl group for the terminal amino hydrogen of ketonethiosemicarbazones improved the activity appreciably. In addition, the double bond in thiosemicarbazones is an important factor for the increment of hydrophobicity. Thus hydrophobic ketonethiosemicarbazones are excellent inhibitors of melanogenesis like aldehydethiosemicarbazones. |
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Keywords: | Aldehydethiosemicarbazones Ketonethiosemicarbazones Melanogenesis inhibition Melanoma B16 |
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