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W1770

Sigma-Aldrich

WR99210

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C14H18Cl3N5O2
CAS Number:
47326-86-3
Molecular Weight:
394.68
MDL number:
MFCD01679034
UNSPSC Code:
12352202
PubChem Substance ID:
329830427
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: 0.2 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

CC1(C)N=C(N)N=C(N)N1OCCCOc2cc(Cl)c(Cl)cc2Cl

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)

InChI key

MJZJYWCQPMNPRM-UHFFFAOYSA-N

Biochem/physiol Actions

WR99210 is a potent inhibitor of Plasmodium falciparum dihydrofolate reductase (DHFR), which is a major malarial drug target. It has subnanomolar potency for the wild type, double mutant and quadruple mutant dihydrofolate reductases.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000042122
0000042125
0000014239
095M4622V
063M4623V

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S Mookherjee et al.
The American journal of tropical medicine and hygiene, 61(1), 131-140 (1999-08-04)
As resistance to chloroquine spreads in sub-Saharan Africa, pyrimethamine plus sulfadoxine (PSD) is increasingly used as a first-line treatment for falciparum malaria. Populations of Plasmodium falciparum (Pf) resistant to PSD have been selected quickly in other regions. The resistance is
Reinaldo Teixeira Delfino et al.
Biophysical chemistry, 98(3), 287-300 (2002-07-20)
The development of drug resistance is reducing the efficiency of antifolates as antimalarials. This phenomenon has been linked to the occurrence of mutations in the parasite's dihydrofolate reductase (DHFR). In this way, the resistance to pyrimethamine and cycloguanil, two potent
Manoj Kumar et al.
Molecular diversity, 14(3), 595-604 (2009-08-22)
The worldwide TB structural genomics initiative has identified several new drug targets for Mycobacterium tuberculosis (M. tb). Dihydrofolate reductase (DHFR) catalyzes the NADPH-dependent reduction of dihydrofolate to tetrahydrofolate that is essential for DNA synthesis. Inhibition of its activity leads to
E G Hankins et al.
Molecular and biochemical parasitology, 117(1), 91-102 (2001-09-12)
We have expressed dhfr alleles of Plasmodium falciparum in the budding yeast, Saccharomyces cerevisiae, and used this yeast model to identify single amino acid substitutions that confer high level pyrimethamine resistance on the background of the triple mutant dhfr (I51+R59+N108).
G Rastelli et al.
Bioorganic & medicinal chemistry, 8(5), 1117-1128 (2000-07-06)
The nature of the interactions between Plasmodium falciparum dihydrofolate reductase (pfDHFR) and antimalarial antifolates, i.e., pyrimethamine (Pyr), cycloguanil (Cyc) and WR99210 including some of their analogues, was investigated by molecular modeling in conjunction with the determination of the inhibition constants
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