BRL 6231 | CAS#30711-93-4 | antimalarial

MedKoo Cat#: 585421 | Name: BRL 6231

Description:

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

BRL 6231 is a triazine antimalarial.

Chemical Structure

BRL 6231

CAS#30711-93-4

Theoretical Analysis

MedKoo Cat#: 585421

Name: BRL 6231

CAS#: 30711-93-4

Chemical Formula: C14H18Cl3N5O2

Exact Mass: 393.0526

Molecular Weight: 394.68

Elemental Analysis: C, 42.61; H, 4.60; Cl, 26.95; N, 17.74; O, 8.11

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

BRL 6231; BRL6231; BRL-6231

IUPAC/Chemical Name

6,6-dimethyl-1-[3-(2,4,5-trichlorophenoxy)propoxy]-1,3,5-triazine-2,4-diamine

InChi Key

MJZJYWCQPMNPRM-UHFFFAOYSA-N

InChi Code

InChI=1S/C14H18Cl3N5O2/c1-14(2)21-12(18)20-13(19)22(14)24-5-3-4-23-11-7-9(16)8(15)6-10(11)17/h6-7H,3-5H2,1-2H3,(H4,18,19,20,21)

SMILES Code

NC1=NC(N)=NC(C)(C)N1OCCCOC2=CC(Cl)=C(Cl)C=C2Cl

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 394.68 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: Knight DJ, Mamalis P, Peters W. The antimalarial activity of N-benzyl-oxydihydrotriazines. III. The activity of 4,6-diamino-1,2-dihydro-2,2-dimethyl-1-(2,4,5,-trichloropropyloxy)-1,3,5-triazine hydrobromide (BRL 51084) and hydrochloride (BRL 6231). Ann Trop Med Parasitol. 1982 Feb;76(1):1-7. PubMed PMID: 7044322. 2: Nettleton MJ, Poyser RH, Shorter JH. The cardiovascular effects of two new triazine antimalarials, BRL 50216 (Clociguanil) and BRL 6231. Toxicol Appl Pharmacol. 1974 Feb;27(2):271-82. PubMed PMID: 4854671. 3: Knight DJ, Williamson P. The antimalarial activity of N-benzyl-oxydihydrotriazines. IV. The development of resistance to BRL 6231 (4,6-diamino-1,2-dihyydro-2-,2-dimethyl-1-(2,4,5-trichloropropyloxy)-1,3,5 triazine hydrochloride) by Plasmodium berghei. Ann Trop Med Parasitol. 1982 Feb;76(1):9-14. PubMed PMID: 7044325. 4: Boucher MJ, Yeh E. Disruption of Apicoplast Biogenesis by Chemical Stabilization of an Imported Protein Evades the Delayed-Death Phenotype in Malaria Parasites. mSphere. 2019 Jan 23;4(1). pii: e00710-18. doi: 10.1128/mSphere.00710-18. PubMed PMID: 30674649; PubMed Central PMCID: PMC6344605. 5: Nixon MR, Saionz KW, Koo MS, Szymonifka MJ, Jung H, Roberts JP, Nandakumar M, Kumar A, Liao R, Rustad T, Sacchettini JC, Rhee KY, Freundlich JS, Sherman DR. Folate pathway disruption leads to critical disruption of methionine derivatives in Mycobacterium tuberculosis. Chem Biol. 2014 Jul 17;21(7):819-30. doi: 10.1016/j.chembiol.2014.04.009. Epub 2014 Jun 19. PubMed PMID: 24954008. 6: Asada M, Yahata K, Hakimi H, Yokoyama N, Igarashi I, Kaneko O, Suarez CE, Kawazu S. Transfection of Babesia bovis by Double Selection with WR99210 and Blasticidin-S and Its Application for Functional Analysis of Thioredoxin Peroxidase-1. PLoS One. 2015 May 11;10(5):e0125993. doi: 10.1371/journal.pone.0125993. eCollection 2015. PubMed PMID: 25962142; PubMed Central PMCID: PMC4427477. 7: Cho S, Yang S, Rhie H. The gene encoding the alternative thymidylate synthase ThyX is regulated by sigma factor SigB in Corynebacterium glutamicum ATCC 13032. FEMS Microbiol Lett. 2012 Mar;328(2):157-65. doi: 10.1111/j.1574-6968.2011.02494.x. Epub 2012 Jan 16. PubMed PMID: 22224900. 8: Kamchonwongpaisan S, Vanichtanankul J, Taweechai S, Chitnumsub P, Yuthavong Y. The role of tryptophan-48 in catalysis and binding of inhibitors of Plasmodium falciparum dihydrofolate reductase. Int J Parasitol. 2007 Jun;37(7):787-93. Epub 2007 Jan 14. PubMed PMID: 17320089. 9: Nirmalan N, Sims PF, Hyde JE. Translational up-regulation of antifolate drug targets in the human malaria parasite Plasmodium falciparum upon challenge with inhibitors. Mol Biochem Parasitol. 2004 Jul;136(1):63-70. PubMed PMID: 15138068. 10: Canfield CJ, Milhous WK, Ager AL, Rossan RN, Sweeney TR, Lewis NJ, Jacobus DP. PS-15: a potent, orally active antimalarial from a new class of folic acid antagonists. Am J Trop Med Hyg. 1993 Jul;49(1):121-6. PubMed PMID: 8352384. 11: Auliff AM, Balu B, Chen N, O'Neil MT, Cheng Q, Adams JH. Functional analysis of Plasmodium vivax dihydrofolate reductase-thymidylate synthase genes through stable transformation of Plasmodium falciparum. PLoS One. 2012;7(7):e40416. doi: 10.1371/journal.pone.0040416. Epub 2012 Jul 9. PubMed PMID: 22792308; PubMed Central PMCID: PMC3392216. 12: Fidock DA, Nomura T, Wellems TE. Cycloguanil and its parent compound proguanil demonstrate distinct activities against Plasmodium falciparum malaria parasites transformed with human dihydrofolate reductase. Mol Pharmacol. 1998 Dec;54(6):1140-7. PubMed PMID: 9855645. 13: Fidock DA, Wellems TE. Transformation with human dihydrofolate reductase renders malaria parasites insensitive to WR99210 but does not affect the intrinsic activity of proguanil. Proc Natl Acad Sci U S A. 1997 Sep 30;94(20):10931-6. PubMed PMID: 9380737; PubMed Central PMCID: PMC23535. 14: Maier AG, Braks JA, Waters AP, Cowman AF. Negative selection using yeast cytosine deaminase/uracil phosphoribosyl transferase in Plasmodium falciparum for targeted gene deletion by double crossover recombination. Mol Biochem Parasitol. 2006 Nov;150(1):118-21. Epub 2006 Jul 25. PubMed PMID: 16901558. 15: Meyer SC, Majumder SK, Cynamon MH. In vitro activities of PS-15, a new dihydrofolate reductase inhibitor, and its cyclic metabolite against Mycobacterium avium complex. Antimicrob Agents Chemother. 1995 Aug;39(8):1862-3. PubMed PMID: 7486934; PubMed Central PMCID: PMC162841. 16: Wooden JM, Hartwell LH, Vasquez B, Sibley CH. Analysis in yeast of antimalaria drugs that target the dihydrofolate reductase of Plasmodium falciparum. Mol Biochem Parasitol. 1997 Mar;85(1):25-40. PubMed PMID: 9108546. 17: Hunt SY, Rezvani BB, Sibley CH. Novel alleles of Plasmodium falciparum dhfr that confer resistance to chlorcycloguanil. Mol Biochem Parasitol. 2005 Jan;139(1):25-32. PubMed PMID: 15610816. 18: Janse CJ, Ramesar J, Waters AP. High-efficiency transfection and drug selection of genetically transformed blood stages of the rodent malaria parasite Plasmodium berghei. Nat Protoc. 2006;1(1):346-56. PubMed PMID: 17406255. 19: Auliff A, Wilson DW, Russell B, Gao Q, Chen N, Anh le N, Maguire J, Bell D, O'Neil MT, Cheng Q. Amino acid mutations in Plasmodium vivax DHFR and DHPS from several geographical regions and susceptibility to antifolate drugs. Am J Trop Med Hyg. 2006 Oct;75(4):617-21. PubMed PMID: 17038682. 20: Hekmat-Nejad M, Rathod PK. Plasmodium falciparum: kinetic interactions of WR99210 with pyrimethamine-sensitive and pyrimethamine-resistant dihydrofolate reductase. Exp Parasitol. 1997 Nov;87(3):222-8. PubMed PMID: 9371087.