TBAJ-876 | CAS#2332841-25-3 | Anti-TB agent

MedKoo Cat#: 465986 | Name: TBAJ-876

Description:

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

TBAJ-876 is a novel anti-tuberculosis (TB) agent, possessing improved safety properties compared to bedaquiline.

Chemical Structure

TBAJ-876

CAS#2332841-25-3 (RS-isomer)

Theoretical Analysis

MedKoo Cat#: 465986

Name: TBAJ-876

CAS#: 2332841-25-3 (RS-isomer)

Chemical Formula: C31H37BrN4O7

Exact Mass: 656.1846

Molecular Weight: 657.56

Elemental Analysis: C, 56.62; H, 5.67; Br, 12.15; N, 8.52; O, 17.03

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

2131784-39-7 (Racemate) 2508131-30-2 (R-isomer) 2731927-36-7 (SR-isomer)

Synonym

TBAJ-876; TBAJ876; TBAJ 876;

IUPAC/Chemical Name

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

InChi Key

HHDDKDPLFXIPBX-DLFZDVPBSA-N

InChi Code

InChI=1S/C31H37BrN4O7/c1-36(2)12-11-31(37,19-15-24(38-3)34-25(16-19)39-4)27(21-17-26(40-5)35-30(43-8)28(21)41-6)22-14-18-13-20(32)9-10-23(18)33-29(22)42-7/h9-10,13-17,27,37H,11-12H2,1-8H3/t27-,31-/m1/s1

SMILES Code

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

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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 657.56 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: Sutherland HS, Lu GL, Tong AST, Conole D, Franzblau SG, Upton AM, Lotlikar MU, Cooper CB, Palmer BD, Choi PJ, Denny WA. Synthesis and structure-activity relationships for a new class of tetrahydronaphthalene amide inhibitors of Mycobacterium tuberculosis. Eur J Med Chem. 2022 Feb 5;229:114059. doi: 10.1016/j.ejmech.2021.114059. Epub 2021 Dec 21. PMID: 34963068; PMCID: PMC8811485. 2: 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. 3: Almeida D, Converse PJ, Li SY, Upton AM, Fotouhi N, Nuermberger EL. Comparative Efficacy of the Novel Diarylquinoline TBAJ-876 and Bedaquiline against a Resistant Rv0678 Mutant in a Mouse Model of Tuberculosis. Antimicrob Agents Chemother. 2021 Nov 17;65(12):e0141221. doi: 10.1128/AAC.01412-21. Epub 2021 Sep 27. PMID: 34570644; PMCID: PMC8597756. 4: Choi PJ, Conole D, Sutherland HS, Blaser A, Tong AST, Cooper CB, Upton AM, Palmer BD, Denny WA. Synthetic Studies to Help Elucidate the Metabolism of the Preclinical Candidate TBAJ-876-A Less Toxic and More Potent Analogue of Bedaquiline. Molecules. 2020 Mar 20;25(6):1423. doi: 10.3390/molecules25061423. PMID: 32245020; PMCID: PMC7144385. 5: Sarathy JP, Ganapathy US, Zimmerman MD, Dartois V, Gengenbacher M, Dick T. TBAJ-876, a 3,5-Dialkoxypyridine Analogue of Bedaquiline, Is Active against Mycobacterium abscessus. Antimicrob Agents Chemother. 2020 Mar 24;64(4):e02404-19. doi: 10.1128/AAC.02404-19. PMID: 31964791; PMCID: PMC7179298. 6: Sarathy JP, Gruber G, Dick T. Re-Understanding the Mechanisms of Action of the Anti-Mycobacterial Drug Bedaquiline. Antibiotics (Basel). 2019 Dec 11;8(4):261. doi: 10.3390/antibiotics8040261. PMID: 31835707; PMCID: PMC6963887. 7: 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. 8: 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. 9: Sarathy JP, Ragunathan P, Cooper CB, Upton AM, Grüber G, Dick T. TBAJ-876 Displays Bedaquiline-Like Mycobactericidal Potency without Retaining the Parental Drug's Uncoupler Activity. Antimicrob Agents Chemother. 2020 Jan 27;64(2):e01540-19. doi: 10.1128/AAC.01540-19. PMID: 31712198; PMCID: PMC6985740. 10: Sarathy JP, Ragunathan P, Shin J, Cooper CB, Upton AM, Grüber G, Dick T. TBAJ-876 Retains Bedaquiline's Activity against Subunits c and ε of Mycobacterium tuberculosis F-ATP Synthase. Antimicrob Agents Chemother. 2019 Sep 23;63(10):e01191-19. doi: 10.1128/AAC.01191-19. PMID: 31358589; PMCID: PMC6761534.