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  • Organocatalytic multicomponent reaction for the acquisition of a selective inhibitor of mPTPB, a virulence factor of tuberculosis.

Organocatalytic multicomponent reaction for the acquisition of a selective inhibitor of mPTPB, a virulence factor of tuberculosis.

Chemical communications (Cambridge, England) (2013-02-06)
Rongjun He, Li-Fan Zeng, Yantao He, Li Wu, Andrea Michelle Gunawan, Zhong-Yin Zhang
ABSTRACT

Mycobacterium protein tyrosine phosphatase B (mPTPB) is essential for the survival and persistence of Mycobacterium in the host. Thus small molecule inhibitors of mPTPB are potential anti-TB agents. We developed an efficient organocatalytic multicomponent reaction (MCR) between pyrrole, formaldehyde and aniline, affording a potent and selective mPTPB inhibitor with an IC(50) value of 1.5 μM and >50-fold specificity. Our studies provide a successful example of using organocatalysis as a discovery tool for the acquisition of PTP inhibitors.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Aniline-4-13C, 99 atom % 13C
Sigma-Aldrich
Aniline-15N, 98 atom % 15N
Sigma-Aldrich
Aniline, ACS reagent, ≥99.5%
Supelco
Aniline, analytical standard
Sigma-Aldrich
Aniline, ReagentPlus®, 99%
Sigma-Aldrich
Aniline-1-13C, 99 atom % 13C
Sigma-Aldrich
Aniline hydrochloride, ≥99%
Supelco
Aniline solution, certified reference material, 5000 μg/mL in methanol