TY - JOUR
T1 - Ketonethiosemicarbazones
T2 - Structure-activity relationships for their melanogenesis inhibition
AU - Thanigaimalai, Pillaiyar
AU - Lee, Ki Cheul
AU - Sharma, Vinay K.
AU - Roh, Eunmiri
AU - Kim, Youngsoo
AU - Jung, Sang Hun
PY - 2011/6/15
Y1 - 2011/6/15
N2 - 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.
AB - 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.
KW - Aldehydethiosemicarbazones
KW - Ketonethiosemicarbazones
KW - Melanogenesis inhibition
KW - Melanoma B16
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UR - http://www.scopus.com/inward/citedby.url?scp=79957853629&partnerID=8YFLogxK
U2 - 10.1016/j.bmcl.2011.04.146
DO - 10.1016/j.bmcl.2011.04.146
M3 - Article
C2 - 21601449
AN - SCOPUS:79957853629
SN - 0960-894X
VL - 21
SP - 3527
EP - 3530
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
IS - 12
ER -
