An update on the compound challenge: 93-02-7

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HPLC of Formula: C9H10O3. In 2019.0 BIOORG CHEM published article about DRUG-RESISTANT TUBERCULOSIS; TRANS-CINNAMIC ACID; PARALLEL SYNTHESIS; DERIVATIVES; INHIBITORS; DOCKING in [Upare, Abhay Atmaram; Gadekar, Pradip K.; Sivaramakrishnan, H.] Piramal Enterprises Ltd, Dept Proc Dev, Lighthall A Wing, Hiranandani Business PK, Sakivihar Rd, Mumbai 400072, Maharashtra, India; [Naik, Nishigandha] Haffkine Inst Training Res & Testing, Acharya Donde MargPorel, Mumbai 400012, Maharashtra, India; [Khedkar, Vijay M.] Shri Vile Parle Kelavani Mandars Inst Pharm, Dept Pharmaceut Chem, Mumbai Agra Natl Hwy, Dhule 424001, Maharashtra, India; [Sarkar, Dhiman; Choudhari, Amit] CSIR, Natl Chem Lab, Combi Chem Bio Resource Ctr, Div Organ Chem, Dr Homi Bhabha Rd, Pune 411008, Maharashtra, India; [Upare, Abhay Atmaram; Roopan, S. Mohana] Vellore Inst Technol, Sch Adv Sci, Dept Chem, Chem Heterocycles & Nat Prod Res Lab, Vellore 632014, Tamil Nadu, India in 2019.0, Cited 26.0. The Name is 2,5-Dimethoxybenzaldehyde. Through research, I have a further understanding and discovery of 93-02-7.

Cinnamic acid and its derivatives are known for anti-tubercular activity. The present study reports the synthesis of cinnamic acid derivatives via bioisosteric replacement of terminal carboxylic acid with oxadiazole. A series of cinnamic acid derivatives (styryl oxadiazoles) were designed and synthesized in good yields by reaction of substituted cinnamic acids (2, 15a-15s) with amidoximes. The synthesized styryl oxadiazoles were evaluated in vitro for anti-tubercular activity against Mycobacterium tuberculosis (Mtb) H37Ra strain. The structure-activity relationship (SAR) study has identified several compounds with mixed anti-tubercular profiles. The compound 32 displayed potent anti-tubercular activity (IC50= 0.045 mu g/mL). Molecular docking studies on mycobacterial enoyl-ACP reductase enzyme corroborated well with the experimental findings providing a platform for structure based hit-to-lead development.

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Reference:
Isothiazole – Wikipedia,
,Isothiazole – ScienceDirect.com