The current research protocol was carried to evaluate biological activity of synthesised new chromane and itsanalogues. New chromane {3,5,7-trihydroxy2-(4-hydroxy benzyl) chroman-4-one} isolated from dried leaves of Dillenia indica Linn, family Dilleniaceae is structurally relating with various reported chroman-4-one derivatives displaying remarkable in-vivo analgesic and anti-inflammatory activity.But the literature reveals that 0.8 – 1.0% yield of pure new chromane was obtained in isolation. Followingreported literature data of synthesis and in-silico study (COX2 binding);synthesized new chromane and its derivatives (SI-SX) were investigated for invivoanalgesic and anti-inflammatory examination respectively.in-vivo analgesic study (Tail immersion and hot plate method) also displayed the significant analgesic potential of new chromane and its O-alkyl substituents (especially SI) while other synthesized compounds (SV-SX) reported for moderate to mild effects w.r.t. reference drug.Moreover, synthetic new chromane and O-alkyl substituent (SI) exhibited maximum anti-inflammatory activity also in terms of increment of paw volume and percentage inhibition of paw edema while others (SV-SX) showed mild antiinflammatory action in comparison to referencedrug.