TBAJ-587 | anti-tuberculosis agent | CAS#2252316-16-6

MedKoo Cat#: 555614 | Name: TBAJ-587

Description:

WARNING: This product is for research use only, not for human or veterinary use.

TBAJ-587 is a potent anti-tuberculosis agent. TBAJ-587 inhibits M.tb strain H37Rv growth with MIC90s of 0.006 and <0.02 µg/mL in MABA and LORA assay, respectively. BAJ-587 has more potent activity against M. tuberculosis and better efficacy in animal models of TB.

Chemical Structure

TBAJ-587

CAS#2252316-16-6 (free base)

Theoretical Analysis

MedKoo Cat#: 555614

Name: TBAJ-587

CAS#: 2252316-16-6 (free base)

Chemical Formula: C30H33BrFN3O5

Exact Mass: 613.1588

Molecular Weight: 614.51

Elemental Analysis: C, 58.64; H, 5.41; Br, 13.00; F, 3.09; N, 6.84; O, 13.02

Price and Availability

Size	Price	Availability
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 Weeks
200mg	USD 1,250.00	2 Weeks
500mg	USD 1,950.00	2 Weeks
1g	USD 2,950.00	2 Weeks
2g	USD 5,450.00	2 Weeks

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Related CAS #

2252316-16-6 (free base) TBAJ-587 HCl

Synonym

TBAJ-587; TBAJ 587; TBAJ587;

IUPAC/Chemical Name

(1S,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-2-(2,6-dimethoxypyridin-4-yl)-4-(dimethylamino)-1-(2-fluoro-3-methoxyphenyl)butan-2-ol

InChi Key

JJEGOJPMKLRSPJ-POURPWNDSA-N

InChi Code

InChI=1S/C30H33BrFN3O5/c1-35(2)13-12-30(36,19-16-25(38-4)34-26(17-19)39-5)27(21-8-7-9-24(37-3)28(21)32)22-15-18-14-20(31)10-11-23(18)33-29(22)40-6/h7-11,14-17,27,36H,12-13H2,1-6H3/t27-,30-/m1/s1

SMILES Code

COC1=C(F)C([C@H](C2=CC3=CC(Br)=CC=C3N=C2OC)[C@](O)(C4=CC(OC)=NC(OC)=C4)CCN(C)C)=CC=C1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 614.51 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Fan J, Tan Z, He S, Li A, Jia Y, Li J, Zhang Z, Li B, Chu H. TBAJ-587, a novel diarylquinoline, is active against Mycobacterium abscessus. Antimicrob Agents Chemother. 2024 Oct 29:e0094524. doi: 10.1128/aac.00945-24. Epub ahead of print. PMID: 39470202. 2: Zhang Y, Lai Y, Zhou S, Ran T, Zhang Y, Zhao Z, Feng Z, Yu L, Xu J, Shi K, Wang J, Pang Y, Li L, Chen H, Guddat LW, Gao Y, Liu F, Rao Z, Gong H. Inhibition of M. tuberculosis and human ATP synthase by BDQ and TBAJ-587. Nature. 2024 Jul;631(8020):409-414. doi: 10.1038/s41586-024-07605-8. Epub 2024 Jul 3. PMID: 38961288. 3: Li S-Y, Tyagi S, Soni H, Betoudji F, Converse PJ, Mdluli K, Upton AM, Fotouhi N, Barros-Aguirre D, Ballell L, Jimenez-Navarro E, Nuermberger EL. Bactericidal and sterilizing activity of novel regimens combining bedaquiline or TBAJ-587 with GSK2556286 and TBA-7371 in a mouse model of tuberculosis. Antimicrob Agents Chemother. 2024 Apr 3;68(4):e0156223. doi: 10.1128/aac.01562-23. Epub 2024 Feb 20. PMID: 38376228; PMCID: PMC10989019. 4: Ahmad T, Gao F, Li J, Zhang Z, Song T, Yuan Q, Zhang W. Synergistic Li/Li Bimetallic System for the Asymmetric Synthesis of Antituberculosis Drug TBAJ-587. J Org Chem. 2023 Jun 2;88(11):7601-7606. doi: 10.1021/acs.joc.3c00705. Epub 2023 May 1. PMID: 37125776; PMCID: PMC10242759. 5: Li SY, Converse PJ, Betoudji F, Lee J, Mdluli K, Upton A, Fotouhi N, Nuermberger EL. Next-Generation Diarylquinolines Improve Sterilizing Activity of Regimens with Pretomanid and the Novel Oxazolidinone TBI-223 in a Mouse Tuberculosis Model. Antimicrob Agents Chemother. 2023 Apr 18;67(4):e0003523. doi: 10.1128/aac.00035-23. Epub 2023 Mar 15. PMID: 36920217; PMCID: PMC10112056. 6: Barbaro L, Nagalingam G, Triccas JA, Tan L, West NP, Priebbenow DL, Baell JB. Discovery of Anti-tubercular Analogues of Bedaquiline with Modified A-, B- and C-Ring Subunits. ChemMedChem. 2023 Jan 3;18(1):e202200533. doi: 10.1002/cmdc.202200533. Epub 2022 Nov 14. PMID: 36259365. 7: Black TA, Buchwald UK. The pipeline of new molecules and regimens against drug-resistant tuberculosis. J Clin Tuberc Other Mycobact Dis. 2021 Nov 5;25:100285. doi: 10.1016/j.jctube.2021.100285. PMID: 34816020; PMCID: PMC8593651. 8: Xu J, Converse PJ, Upton AM, Mdluli K, Fotouhi N, Nuermberger EL. Comparative Efficacy of the Novel Diarylquinoline TBAJ-587 and Bedaquiline against a Resistant Rv0678 Mutant in a Mouse Model of Tuberculosis. Antimicrob Agents Chemother. 2021 Mar 18;65(4):e02418-20. doi: 10.1128/AAC.02418-20. PMID: 33526488; PMCID: PMC8097419. 9: Sutherland HS, Tong AST, Choi PJ, Blaser A, Franzblau SG, Cooper CB, Upton AM, Lotlikar M, Denny WA, Palmer BD. Variations in the C-unit of bedaquiline provides analogues with improved biology and pharmacology. Bioorg Med Chem. 2020 Jan 1;28(1):115213. doi: 10.1016/j.bmc.2019.115213. Epub 2019 Nov 26. PMID: 31810890. 10: Kamariah N, Ragunathan P, Shin J, Saw WG, Wong CF, Dick T, Grüber G. Unique structural and mechanistic properties of mycobacterial F-ATP synthases: Implications for drug design. Prog Biophys Mol Biol. 2020 May;152:64-73. doi: 10.1016/j.pbiomolbio.2019.11.006. Epub 2019 Nov 16. PMID: 31743686.