Antioxidant may provide anti-arthritic effect that contributes to resolution of inflammation. Gallic acid (GA) and its derivatives were reported to be effective in treatment of arthritis. But GA-suppressed cell proliferation may compromise its effect on chondro-protection. In this study, we synthesized sulfonamido-based gallate-JEZTC and investigated its effect on rabbit articular chondrocytes through examination of the cell proliferation, morphology, viability, glycosaminoglycan (GAG) synthesis, and cartilage-specific gene expression. Results showed that JEZTC could effectively promote chondrocyte growth and enhance secretion and synthesis of cartilage extracellular matrix (ECM) by upregulating expression levels of aggrecan, collagen II, and Sox9 genes. Expression of collagen I which marked chondrocyte dedifferentiation was effectively downregulated by JEZTC. In addition, hypertrophy that may lead to chondrocyte ossification could not be detected in JEZTC groups. The results indicated JEZTC can well preserve the phenotype of chondrocytes. Range of 2.344 to 9.375 μg/ml is the recommended dose of JEZTC, which showed increased cell proliferation. Especially, JEZTC of 4.688 μg/ml showed the best performance. This study might provide a basis for development of a novel agent for the treatment of symptomatic chondral and osteochondral lesions.