Tebuquine | CI-897 | CAS#74129-03-6 | novel amodiaquine congener

MedKoo Cat#: 526427 | Name: Tebuquine

Description:

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

Tebuquine, also known CI-897 and WR-228258, is an antimalarial agent. WR-225,448 is active against P. falciparum in vitro. WR 228,258 in vitro shows a chloroquine-like effect, but not in vivo, suggesting that its mode of action in vivo is different from that of chloroquine. WR 225,448 has no action in the CIPC in vitro and affects primarily mitochondria of the parasites in vivo. It probably acts through a metabolite. Both pre-erythrocytic and erythrocytic stages of rodent malaria parasites are affected by WR 225,448.

Chemical Structure

Tebuquine

CAS#74129-03-6

Theoretical Analysis

MedKoo Cat#: 526427

Name: Tebuquine

CAS#: 74129-03-6

Chemical Formula: C26H25Cl2N3O

Exact Mass: 465.1375

Molecular Weight: 466.41

Elemental Analysis: C, 66.96; H, 5.40; Cl, 15.20; N, 9.01; O, 3.43

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.

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Related CAS #

No Data

Synonym

Tebuquine; CI-897; CI897; CI 897; WR-228,258; WR 228,258; WR228,258; WR-228258; WR 228258; WR228258.

IUPAC/Chemical Name

(1,1'-Biphenyl)-2-ol, 4'-chloro-5-((7-chloro-4-quinolinyl)amino)-3-(((1,1-dimethylethyl)amino)methyl)-

InChi Key

BCHMRNALCJISMZ-UHFFFAOYSA-N

InChi Code

InChI=1S/C26H25Cl2N3O/c1-26(2,3)30-15-17-12-20(14-22(25(17)32)16-4-6-18(27)7-5-16)31-23-10-11-29-24-13-19(28)8-9-21(23)24/h4-14,30,32H,15H2,1-3H3,(H,29,31)

SMILES Code

OC1=C(CNC(C)(C)C)C=C(NC2=CC=NC3=CC(Cl)=CC=C23)C=C1C4=CC=C(Cl)C=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

Soluble in DMSO

Shelf Life

>2 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 466.41 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: Romero AH, Acosta ME, Gamboa N, Charris JE, Salazar J, López SE. Synthesis, β-hematin inhibition studies and antimalarial evaluation of dehydroxy isotebuquine derivatives against Plasmodium berghei. Bioorg Med Chem. 2015 Aug 1;23(15):4755-62. doi: 10.1016/j.bmc.2015.05.040. PubMed PMID: 26081761. 2: Casagrande M, Basilico N, Parapini S, Romeo S, Taramelli D, Sparatore A. Novel amodiaquine congeners as potent antimalarial agents. Bioorg Med Chem. 2008 Jul 15;16(14):6813-23. doi: 10.1016/j.bmc.2008.05.068. PubMed PMID: 18562202. 3: Sharma P, Chhabra S, Rai N, Ghoshal N. Exploration of rate-limiting conformational state for 5-[(7-chloro-4-quinolinyl)amino]-3-[(alkylamino)methyl][1,1'-biphenyl]-2-ols and N(omega)-oxides (tebuquine analogues) for antimalarial activity using molecular shape analysis and molecular field analysis studies. J Chem Inf Model. 2007 May-Jun;47(3):1087-96. PubMed PMID: 17425301. 4: Miroshnikova OV, Hudson TH, Gerena L, Kyle DE, Lin AJ. Synthesis and antimalarial activity of new isotebuquine analogues. J Med Chem. 2007 Feb 22;50(4):889-96. PubMed PMID: 17266295. 5: Naisbitt DJ, Williams DP, O'Neill PM, Maggs JL, Willock DJ, Pirmohamed M, Park BK. Metabolism-dependent neutrophil cytotoxicity of amodiaquine: A comparison with pyronaridine and related antimalarial drugs. Chem Res Toxicol. 1998 Dec;11(12):1586-95. PubMed PMID: 9860505. 6: Ruscoe JE, Tingle MD, O'Neill PM, Ward SA, Park BK. Effect of disposition of mannich antimalarial agents on their pharmacology and toxicology. Antimicrob Agents Chemother. 1998 Sep;42(9):2410-6. PubMed PMID: 9736572; PubMed Central PMCID: PMC105842. 7: O'Neill PM, Willock DJ, Hawley SR, Bray PG, Storr RC, Ward SA, Park BK. Synthesis, antimalarial activity, and molecular modeling of tebuquine analogues. J Med Chem. 1997 Feb 14;40(4):437-48. PubMed PMID: 9046333. 8: Peters W, Robinson BL. The chemotherapy of rodent malaria. XLVII. Studies on pyronaridine and other Mannich base antimalarials. Ann Trop Med Parasitol. 1992 Oct;86(5):455-65. PubMed PMID: 1288426. 9: Werbel LM, Cook PD, Elslager EF, Hung JH, Johnson JL, Kesten SJ, McNamara DJ, Ortwine DF, Worth DF. Synthesis, antimalarial activity, and quantitative structure-activity relationships of tebuquine and a series of related 5-[(7-chloro-4-quinolinyl)amino]-3-[(alkylamino)methyl] [1,1'-biphenyl]-2-ols and N omega-oxides. J Med Chem. 1986 Jun;29(6):924-39. PubMed PMID: 3712383. 10: Peters W, Robinson BL. The chemotherapy of rodent malaria, XXXVII. The in vivo action of two Mannich bases, WR 194,965 and WR 228,258 and an 8-aminoquinoline WR 225,448. Ann Trop Med Parasitol. 1984 Dec;78(6):561-5. PubMed PMID: 6532327. 11: Peters W, Irare SG, Ellis DS, Warhurst DC, Robinson BL. The chemotherapy of rodent malaria, XXXVIII. Studies on the activity of three new antimalarials (WR 194,965, WR 228,258 and WR 225,448) against rodent and human malaria parasites (Plasmodium berghei and P. falciparum). Ann Trop Med Parasitol. 1984 Dec;78(6):567-79. PubMed PMID: 6398032.