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MedKoo Cat#: 558444 | Name: HEPT

Description:

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

HEPT is a non-nucleoside HIV-1 reverse transcription inhibitor

Chemical Structure

HEPT
HEPT
CAS#123027-56-5

Theoretical Analysis

MedKoo Cat#: 558444

Name: HEPT

CAS#: 123027-56-5

Chemical Formula: C14H16N2O4S

Exact Mass: 308.0800

Molecular Weight: 308.35

Elemental Analysis: C, 54.53; H, 5.23; N, 9.09; O, 20.75; S, 10.40

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 #
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Synonym
HEPT;
IUPAC/Chemical Name
1-[(2-Hydroxyethoxy)methyl]-6-(phenylthio)thymine
InChi Key
HDMHBHNRWDNNCD-UHFFFAOYSA-N
InChi Code
InChI=1S/C14H16N2O4S/c1-10-12(18)15-14(19)16(9-20-8-7-17)13(10)21-11-5-3-2-4-6-11/h2-6,17H,7-9H2,1H3,(H,15,18,19)
SMILES Code
O=C(N1)N(COCCO)C(SC2=CC=CC=C2)=C(C)C1=O
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 308.35 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.

Recalculate based on batch purity %
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: Nuter F, Dimé AK, Chen C, Bounaadja L, Mouray E, Florent I, Six Y, Buriez O, Marinetti A, Voituriez A. Access to new endoperoxide derivatives by electrochemical oxidation of substituted 3-azabicyclo[4.1.0]hept-4-enes. Chemistry. 2015 Mar 27;21(14):5584-93. doi: 10.1002/chem.201406138. Epub 2015 Feb 20. PubMed PMID: 25703453. 2: Hudkins RL, Becknell NC, Lyons JA, Aimone LD, Olsen M, Haltiwanger RC, Mathiasen JR, Raddatz R, Gruner JA. 3,4-Diaza-bicyclo[4.1.0]hept-4-en-2-one phenoxypropylamine analogs of irdabisant (CEP-26401) as potent histamine-3 receptor inverse agonists with robust wake-promoting activity. Eur J Med Chem. 2015 May 5;95:349-56. doi: 10.1016/j.ejmech.2015.03.054. Epub 2015 Mar 24. PubMed PMID: 25827402. 3: Scognamiglio J, Letizia CS, Api AM. Fragrance material review on 1-(3,3-dimethylbicyclo[2.2.1]hept-2-yl)ethane-1-one. Food Chem Toxicol. 2013 Dec;62 Suppl 1:S110-4. doi: 10.1016/j.fct.2013.08.058. Review. PubMed PMID: 24246178. 4: Zhu S, Ren L, Yu S, Gong C, Song D, Zheng G. Enzymatic preparation of optically pure (+)-2-azabicyclo[2.2.1]hept-5-en-3-one by (-)-γ-lactamase from Bradyrhizobium japonicum USDA 6. Bioorg Med Chem Lett. 2014 Oct 15;24(20):4899-902. doi: 10.1016/j.bmcl.2014.08.057. Epub 2014 Sep 2. PubMed PMID: 25240615. 5: Wałejko P, Dąbrowski M, Szczepaniak L, Morzycki JW, Witkowski S. Stereochemistry of ring-opening/cross metathesis reactions of exo- and endo-7-oxabicyclo[2.2.1]hept-5-ene-2-carbonitriles with allyl alcohol and allyl acetate. Beilstein J Org Chem. 2015 Oct 13;11:1893-901. doi: 10.3762/bjoc.11.204. eCollection 2015. PubMed PMID: 26664608; PubMed Central PMCID: PMC4661012. 6: Toropova AP, Toropov AA, Veselinović JB, Miljković FN, Veselinović AM. QSAR models for HEPT derivates as NNRTI inhibitors based on Monte Carlo method. Eur J Med Chem. 2014 Apr 22;77:298-305. doi: 10.1016/j.ejmech.2014.03.013. Epub 2014 Mar 11. PubMed PMID: 24657566. 7: Zhang Y, Ghiassi KB, Deng Q, Samoylova NA, Olmstead MM, Balch AL, Popov AA. Synthesis and structure of LaSc2N@C(s)(hept)-C80 with one heptagon and thirteen pentagons. Angew Chem Int Ed Engl. 2015 Jan 7;54(2):495-9. doi: 10.1002/anie.201409094. Epub 2014 Nov 20. PubMed PMID: 25413484. 8: Safont VS, González-Navarrete P, Oliva M, Andrés J. Inquiry of the electron density transfers in chemical reactions: a complete reaction path for the denitrogenation process of 2,3-diazabicyclo[2.2.1]hept-2-ene derivatives. Phys Chem Chem Phys. 2015 Dec 28;17(48):32358-74. doi: 10.1039/c5cp05518k. PubMed PMID: 26584857. 9: Xin X, Wang H, Li X, Wang D, Wan B. Base-Catalyzed Selective Synthesis of 2-Azabicyclo[3.2.0]hept-2-enes and Sulfonyl Vinyl-Substituted Pyrroles from 3-Aza-1,5-enynes. Org Lett. 2015 Aug 21;17(16):3944-7. doi: 10.1021/acs.orglett.5b01474. Epub 2015 Aug 7. PubMed PMID: 26251020. 10: Hudkins RL, Josef KA, Becknell NC, Aimone LD, Lyons JA, Mathiasen JR, Gruner JA, Raddatz R. Discovery of (1R,6S)-5-[4-(1-cyclobutyl-piperidin-4-yloxy)-phenyl]-3,4-diaza-bicyclo[4.1.0]hep t-4-en-2-one (R,S-4a): histamine H(3) receptor inverse agonist demonstrating potent cognitive enhancing and wake promoting activity. Bioorg Med Chem Lett. 2014 Mar 1;24(5):1303-6. doi: 10.1016/j.bmcl.2014.01.061. Epub 2014 Jan 30. PubMed PMID: 24513042. 11: Chen W, Zhan P, Wu J, Li Z, Liu X. The development of HEPT-type HIV non-nucleoside reverse transcriptase inhibitors and its implications for DABO family. Curr Pharm Des. 2012;18(27):4165-86. Review. PubMed PMID: 22621244. 12: Chatterjee S, Ghadigaonkar S, Sur P, Sharma A, Chattopadhyay S. A chemoenzymatic synthesis of hept-6-ene-2,5-diol stereomers: application to asymmetric synthesis of decarestrictine L, pyrenophorol, and stagonolide E. J Org Chem. 2014 Sep 5;79(17):8067-76. doi: 10.1021/jo5012575. Epub 2014 Aug 19. PubMed PMID: 25116794. 13: Deng Q, Popov AA. Prato and Bingel-Hirsch cycloaddition to heptagon-containing LaSc2N@C(s)(hept)-C80: importance of pentalene units. Chem Commun (Camb). 2015 Apr 4;51(26):5637-40. doi: 10.1039/c5cc00296f. PubMed PMID: 25704065. 14: Chen CH, Abella L, Cerón MR, Guerrero-Ayala MA, Rodríguez-Fortea A, Olmstead MM, Powers XB, Balch AL, Poblet JM, Echegoyen L. Zigzag Sc(2)C(2) Carbide Cluster inside a [88]Fullerene Cage with One Heptagon, Sc(2)C(2)@C(s)(hept)-C(88): A Kinetically Trapped Fullerene Formed by C(2) Insertion? J Am Chem Soc. 2016 Oct 5;138(39):13030-13037. Epub 2016 Sep 21. PubMed PMID: 27592501. 15: Bats JW, Schell P, Engels JW. 5-[(1R,2R,4R)-2-Meth-oxy-1,7,7-tri-methylbi-cyclo-[2.2.1]hept-2-yl]-1H-tetra-zole . Acta Crystallogr Sect E Struct Rep Online. 2013 Jun 8;69(Pt 7):o1028. doi: 10.1107/S1600536813014700. eCollection 2013. PubMed PMID: 24046608; PubMed Central PMCID: PMC3772465. 16: Rosenberg MG, Schrievers T, Brinker UH. Competitive 1,2-C Atom Shifts in the Strained Carbene Spiro[3.3]hept-1-ylidene Explained by Distinct Ring-Puckered Conformers. J Org Chem. 2016 Dec 16;81(24):12388-12400. Epub 2016 Dec 8. PubMed PMID: 27978720. 17: Oh HM, Park JE, Kim J, Kim JH, Kang YK, Chung YK. Pd-catalyzed cycloisomerization of 4-aza-1,6-enynes to 3-aza-bicyclo[4.1.0]hept-2-enes. Chemistry. 2014 Jul 14;20(29):9024-36. doi: 10.1002/chem.201402087. Epub 2014 Jun 25. PubMed PMID: 24965708. 18: Puerto Galvis CE, Kouznetsov VV. An unexpected formation of the novel 7-oxa-2-azabicyclo[2.2.1]hept-5-ene skeleton during the reaction of furfurylamine with maleimides and their bioprospection using a zebrafish embryo model. Org Biomol Chem. 2013 Jan 21;11(3):407-11. doi: 10.1039/c2ob26699g. Epub 2012 Nov 28. PubMed PMID: 23192531. 19: Jasiński R. First example of stepwise, zwitterionic mechanism for bicyclo[2.2.1]hept-5-ene (norbornene) formation process catalyzed by the 1-butyl-3-methylimidazolium cations. Monatsh Chem. 2016;147:1207-1213. Epub 2016 Mar 30. PubMed PMID: 27358502; PubMed Central PMCID: PMC4899506. 20: Chen X, Day DP, Teo WT, Chan PW. Gold- and Brønsted Acid-Catalyzed Cycloisomerization of 1,8-Diynyl Vinyl Acetates to Bicyclo[2.2.1]hept-2-en-7-ones. Org Lett. 2016 Nov 18;18(22):5936-5939. Epub 2016 Oct 28. PubMed PMID: 27791382.