title: Synthesis of novel 1,2-benzothiazine 1,1-dioxide-3-ethanone oxime N-aryl acetamide ether derivatives as potent anti-inflammatory agents and inhibitors of monocyte-to-macrophage transformation.
abstract: A series of novel 1,2-benzothiazine 1,1-dioxide-3-ethanone oxime N-aryl acetamide ether derivatives 7a-h and 9a-h were synthesized starting from sodium salt of saccharin 1 in series of steps. Final compounds 7a-h and 9a-h were evaluated for the anti-inflammatory activity and their ability to inhibit monocyte-to-macrophage transformation. Compounds 7e, 9b, 9e and 9h showed impressive anti-inflammatory activities (TNF-α, IL-8 and MCP-1) at micro molar concentration which was found to be better than positive control i.e., piroxicam. Compound 9e marginally and compound 9h significantly inhibited PMA-induced MMP-9 gelatinase activity. Also compounds 9e and 9h greatly inhibited the PMA-induced monocyte-to-macrophage transformation, a pre-requisite step in the formation of atheroma.
authors: Fluoroorganic Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500607, India.
authors: Malla Reddy
authors: MR
authors: Gannarapu
authors: Centre for Chemical Biology, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500607, India.
authors: Sathish Babu
authors: SB
authors: Vasamsetti
authors: Fluoroorganic Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500607, India.
authors: Nagender
authors: N
authors: Punna
authors: Fluoroorganic Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500607, India.
authors: Naresh Kumar
authors: NK
authors: Royya
authors: Fluoroorganic Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500607, India.
authors: Shanthan Rao
authors: SR
authors: Pamulaparthy
authors: Centre for X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500607, India.
authors: Jagadeesh Babu
authors: JB
authors: Nanubolu
authors: Centre for Chemical Biology, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500607, India. Electronic address: giridhar@iict.res.in.
authors: Srigiridhar
authors: S
authors: Kotamraju
authors: Fluoroorganic Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500607, India. Electronic address: narsaiah@iict.res.in.
authors: Narsaiah
authors: N
authors: Banda
mesh_terms: D000081:Acetamides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D004987:Ethers / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D016209:Interleukin-8 / Q000276:immunology; D008264:Macrophages / Q000187:drug effects* / Q000276:immunology; D020780:Matrix Metalloproteinase 9 / Q000276:immunology; D008958:Models, Molecular; D009000:Monocytes / Q000187:drug effects* / Q000276:immunology; D010091:Oximes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D014409:Tumor Necrosis Factor-alpha / Q000276:immunology
chemical_list: D000081:Acetamides; D000893:Anti-Inflammatory Agents; D004987:Ethers; D016209:Interleukin-8; D010091:Oximes; D014409:Tumor Necrosis Factor-alpha; D020780:Matrix Metalloproteinase 9
keywords: Anti-inflammatory activity; N-aryl acetamide; Oxime ether; PMA-phorbol 12-myristate 13-acetate