TAM16 | CAS#unknown | MTB Pks13 benzofuran inhibitor

MedKoo Cat#: 464527 | Name: TAM16

Description:

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

TAM16 is a benzofuran inhibitor of MTB Pks13 with potent in vitro bactericidal activity against drug-susceptible and drug-resistant clinical isolates of M. tuberculosis. In multiple mouse infection models it showed in vivo efficacy equal to the first-line TB drug isoniazid.

Chemical Structure

TAM16

CAS#unknown

Theoretical Analysis

MedKoo Cat#: 464527

Name: TAM16

CAS#: unknown

Chemical Formula: C22H24N2O4

Exact Mass: 380.1736

Molecular Weight: 380.44

Elemental Analysis: C, 69.46; H, 6.36; N, 7.36; O, 16.82

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 #

No Data

Synonym

TAM16; TAM 16; TAM-16;

IUPAC/Chemical Name

5-hydroxy-2-(4-hydroxyphenyl)-N-methyl-4-(piperidin-1-ylmethyl)benzofuran-3-carboxamide

InChi Key

PQGCMFVNJWTUFH-UHFFFAOYSA-N

InChi Code

InChI=1S/C22H24N2O4/c1-23-22(27)20-19-16(13-24-11-3-2-4-12-24)17(26)9-10-18(19)28-21(20)14-5-7-15(25)8-6-14/h5-10,25-26H,2-4,11-13H2,1H3,(H,23,27)

SMILES Code

O=C(C1=C(C2=CC=C(O)C=C2)OC3=C1C(CN4CCCCC4)=C(O)C=C3)NC

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 380.44 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: Zhao W, Wang B, Liu Y, Fu L, Sheng L, Zhao H, Lu Y, Zhang D. Design, synthesis, and biological evaluation of novel 4H-chromen-4-one derivatives as antituberculosis agents against multidrug-resistant tuberculosis. Eur J Med Chem. 2020 Mar 1;189:112075. doi: 10.1016/j.ejmech.2020.112075. Epub 2020 Jan 19. PMID: 31986405. 2: Gao F, Ye L, Wang Y, Kong F, Zhao S, Xiao J, Huang G. Benzofuran-isatin hybrids and their in vitro anti-mycobacterial activities against multi-drug resistant Mycobacterium tuberculosis. Eur J Med Chem. 2019 Dec 1;183:111678. doi: 10.1016/j.ejmech.2019.111678. Epub 2019 Sep 5. PMID: 31525660. 3: Çınaroğlu SS, Timuçin E. Insights into an alternative benzofuran binding mode and novel scaffolds of polyketide synthase 13 inhibitors. J Mol Model. 2019 Apr 25;25(5):130. doi: 10.1007/s00894-019-4010-y. PMID: 31025202. 4: Gao F, Chen Z, Ma L, Qiu L, Lin J, Lu G. Benzofuran-isatin hybrids tethered via different length alkyl linkers and their in vitro anti-mycobacterial activities. Bioorg Med Chem. 2019 Jun 15;27(12):2652-2656. doi: 10.1016/j.bmc.2019.04.017. Epub 2019 Apr 10. PMID: 30992202. 5: Zhang W, Lun S, Liu LL, Xiao S, Duan G, Gunosewoyo H, Yang F, Tang J, Bishai WR, Yu LF. Identification of Novel Coumestan Derivatives as Polyketide Synthase 13 Inhibitors against Mycobacterium tuberculosis. Part II. J Med Chem. 2019 Apr 11;62(7):3575-3589. doi: 10.1021/acs.jmedchem.9b00010. Epub 2019 Mar 27. PMID: 30875203. 6: Gao F, Yang H, Lu T, Chen Z, Ma L, Xu Z, Schaffer P, Lu G. Design, synthesis and anti-mycobacterial activity evaluation of benzofuran-isatin hybrids. Eur J Med Chem. 2018 Nov 5;159:277-281. doi: 10.1016/j.ejmech.2018.09.049. Epub 2018 Sep 18. PMID: 30296686. 7: Zheng HX, Shan XH, Qu JP, Kang YB. Strategy for Overcoming Full Reversibility of Intermolecular Radical Addition to Aldehydes: Tandem C-H and C-O Bonds Cleaving Cyclization of (Phenoxymethyl)arenes with Carbonyls to Benzofurans. Org Lett. 2018 Jun 1;20(11):3310-3313. doi: 10.1021/acs.orglett.8b01207. Epub 2018 May 18. PMID: 29775071. 8: Cruz JN, Costa JFS, Khayat AS, Kuca K, Barros CAL, Neto AMJC. Molecular dynamics simulation and binding free energy studies of novel leads belonging to the benzofuran class inhibitors of Mycobacterium tuberculosis Polyketide Synthase 13. J Biomol Struct Dyn. 2019 Apr;37(6):1616-1627. doi: 10.1080/07391102.2018.1462734. Epub 2018 May 4. PMID: 29633908. 9: Aggarwal A, Parai MK, Shetty N, Wallis D, Woolhiser L, Hastings C, Dutta NK, Galaviz S, Dhakal RC, Shrestha R, Wakabayashi S, Walpole C, Matthews D, Floyd D, Scullion P, Riley J, Epemolu O, Norval S, Snavely T, Robertson GT, Rubin EJ, Ioerger TR, Sirgel FA, van der Merwe R, van Helden PD, Keller P, Böttger EC, Karakousis PC, Lenaerts AJ, Sacchettini JC. Development of a Novel Lead that Targets M. tuberculosis Polyketide Synthase 13. Cell. 2017 Jul 13;170(2):249-259.e25. doi: 10.1016/j.cell.2017.06.025. Epub 2017 Jun 29. PMID: 28669536; PMCID: PMC5509550.