1. Academic Validation
  2. Synthesis of N-arylindazole-3-carboxamide and N-benzoylindazole derivatives and their evaluation against α-MSH-stimulated melanogenesis

Synthesis of N-arylindazole-3-carboxamide and N-benzoylindazole derivatives and their evaluation against α-MSH-stimulated melanogenesis

  • Bioorg Med Chem Lett. 2019 Sep 15;29(18):2604-2608. doi: 10.1016/j.bmcl.2019.07.055.
Sateesh Kumar Arepalli 1 Chaerim Lee 1 Jae-Kyung Jung 1 Youngsoo Kim 1 Kiho Lee 2 Heesoon Lee 3
Affiliations

Affiliations

  • 1 College of Pharmacy, Chungbuk National University, Chungbuk 28160, Republic of Korea.
  • 2 College of Pharmacy, Korea University, Sejong 30019, Republic of Korea.
  • 3 College of Pharmacy, Chungbuk National University, Chungbuk 28160, Republic of Korea. Electronic address: medchem@chungbuk.ac.kr.
Abstract

We have designed and synthesized twenty-six N-arylindazole-3-carboxamide (3a-p) and N-benzoylindazole (6a-j) derivatives to discover with excellent inhibition activities of α-MSH-stimulated melanogenesis. In the bio evaluation studies of these compounds, we discovered eighteen compounds, out of twenty-six exhibited more potent inhibition than the positive control arbutin. From the SAR studies, we identified 3k and 6g as lead compounds which displayed almost 5 and 9 times more potent inhibition of α-MSH-stimulated melanogenesis respectively than the reference arbutin. It is also evident the presence of electron withdrawing group at para position (R3) for the compounds (3a-p) and presence of +M group at ortho position (R5) for the compounds (6a-j) were crucial for their excellent inhibition activities of α-MSH-stimulated melanogenesis.

Keywords

Arbutin; Melanogenesis; N-Arylindazole-3-carboxamides; N-Benzoylindazoles; α-MSH.

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