Synonym
HI-236; HI 236; HI236; D-PBT; D PBT; DPBT;
IUPAC/Chemical Name
1-(5-Bromopyridin-2-yl)-3-[2-(2,5-dimethoxyphenyl)ethyl]thiourea
InChi Key
GNLVRKKIIIVZHZ-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H18BrN3O2S/c1-21-13-4-5-14(22-2)11(9-13)7-8-18-16(23)20-15-6-3-12(17)10-19-15/h3-6,9-10H,7-8H2,1-2H3,(H2,18,19,20,23)
SMILES Code
S=C(NCCC1=CC(OC)=CC=C1OC)NC2=NC=C(Br)C=C2
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
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
396.30
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: Younis Y, Hunter R, Muhanji CI, Hale I, Singh R, Bailey CM, Sullivan TJ, Anderson KS. [d4U]-spacer-[HI-236] double-drug inhibitors of HIV-1 reverse-transcriptase. Bioorg Med Chem. 2010 Jul 1;18(13):4661-73. doi: 10.1016/j.bmc.2010.05.025. Epub 2010 May 11. PubMed PMID: 20605472; PubMed Central PMCID: PMC2964380.
2: Hunter R, Younis Y, Muhanji CI, Curtin TL, Naidoo KJ, Petersen M, Bailey CM, Basavapathruni A, Anderson KS. C-2-aryl O-substituted HI-236 derivatives as non-nucleoside HIV-1 reverse-transcriptase inhibitors. Bioorg Med Chem. 2008 Dec 15;16(24):10270-80. doi: 10.1016/j.bmc.2008.10.048. Epub 2008 Nov 1. PubMed PMID: 18996020; PubMed Central PMCID: PMC2639753.
3: Hunter R, Muhanji CI, Hale I, Bailey CM, Basavapathruni A, Anderson KS. [d4U]-butyne-[HI-236] as a non-cleavable, bifunctional NRTI/NNRTI HIV-1 reverse-transcriptase inhibitor. Bioorg Med Chem Lett. 2007 May 1;17(9):2614-7. Epub 2007 Feb 4. PubMed PMID: 17317163.
4: Mao C, Sudbeck EA, Venkatachalam TK, Uckun FM. Rational design of N-[2-(2,5-dimethoxyphenylethyl)]-N'-[2-(5-bromopyridyl)]-thiourea (HI-236) as a potent non-nucleoside inhibitor of drug-resistant human immunodeficiency virus. Bioorg Med Chem Lett. 1999 Jun 7;9(11):1593-8. PubMed PMID: 10386942.
5: Chen CL, Venkatachalam TK, Waurzyniak B, Chelstrom L, Uckun FM. In vivo toxicity, pharmacokinetic features and tissue distribution of N-[2-(2,5-dimethoxyphenylethyl)]-N'-[2-(5-bromopyridyl)]-thiourea (HI-236), a potent non-nucleoside inhibitor of HIV-1 reverse transcriptase. Arzneimittelforschung. 2001;51(7):574-81. PubMed PMID: 11505789.
6: Mao C, Sudbeck EA, Venkatachalam TK, Uckun FM. Structure-based design of non-nucleoside reverse transcriptase inhibitors of drug-resistant human immunodeficiency virus. Antivir Chem Chemother. 1999 Sep;10(5):233-40. PubMed PMID: 10574178.
7: D'Cruz OJ, Uckun FM. Discovery of 2,5-dimethoxy-substituted 5-bromopyridyl thiourea (PHI-236) as a potent broad-spectrum anti-human immunodeficiency virus microbicide. Mol Hum Reprod. 2005 Oct;11(10):767-77. Epub 2005 Oct 27. PubMed PMID: 16254003.
8: D'Cruz OJ, Uckun FM. Novel derivatives of phenethyl-5-bromopyridylthiourea and dihydroalkoxybenzyloxopyrimidine are dual-function spermicides with potent anti-human immunodeficiency virus activity. Biol Reprod. 1999 Jun;60(6):1419-28. PubMed PMID: 10330101.
