Quinoxaline | CAS#91-19-0

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

MedKoo CAT#: 329683

CAS#: 91-19-0

Description: Quinoxaline, also called a benzopyrazine, in organic chemistry, is a heterocyclic compound containing a ring complex made up of a benzene ring and a pyrazine ring. It is a colorless oil that melts just above room temperature. Although quinoxaline itself is mainly of academic interest, quinoxaline derivatives are used as dyes, pharmaceuticals, and antibiotics such as olaquindox, carbadox, echinomycin, levomycin and actinoleutin.

Chemical Structure

Quinoxaline

CAS# 91-19-0

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 329683
Name: Quinoxaline
CAS#: 91-19-0
Chemical Formula: C8H6N2
Exact Mass: 130.05
Molecular Weight: 130.150
Elemental Analysis: C, 73.83; H, 4.65; N, 21.52

Price and Availability

Size	Price	Availability
5g	USD 150	2 weeks
10g	USD 250	2 weeks
25g	USD 350	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Quinoxaline; AI3-21308; AI3 21308; AI321308

IUPAC/Chemical Name: 1,4-Benzodiazine

InChi Key: XSCHRSMBECNVNS-UHFFFAOYSA-N

InChi Code: InChI=1S/C8H6N2/c1-2-4-8-7(3-1)9-5-6-10-8/h1-6H

SMILES Code: C12=CC=CC=C1N=CC=N2

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: To be determined

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

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Product Data:

Product Data

Instruction:

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Biological target:	Quinoxaline and its analogs have been investigated as catalyst ligands.
In vitro activity:	A series of novel histone deacetylase (HDAC) inhibitors derived from 3-(benzazol-2-yl)quinoxaline derivatives were designed and synthesized in this study. In vitro results showed that compound 10c had the most potent cytotoxicity, especially in HCT-116 cells with an IC50 value of 0.91 μM, superior to Vorinostat (5.66 μM). These results highlight the great potential of 10c to become a promising anti-cancer HDAC inhibitor. Reference: Bioorg Med Chem Lett. 2023 May 15;88:129305. https://pubmed.ncbi.nlm.nih.gov/37116762/
In vivo activity:	15-Prostaglandin dehydrogenase (15-PGDH) regulates the concentration of prostaglandin E2 in vivo. Inhibitors of 15-PGDH elevate PGE2 levels and promote tissue repair and regeneration. This study describes a novel class of quinoxaline amides that show potent inhibition of 15-PGDH, good oral bioavailability, and protective activity in mouse models of ulcerative colitis and recovery from bone marrow transplantation. Reference: J Med Chem. 2022 Nov 24;65(22):15327-15343. https://pubmed.ncbi.nlm.nih.gov/36322935/

Preparing Stock Solutions

The following data is based on the product molecular weight 130.15 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

Formulation protocol:	1. Yang Y, Liu Q, Wang X, Gou S. Design, synthesis, and biological evaluation of novel HDAC inhibitors with a 3-(benzazol-2-yl)quinoxaline framework. Bioorg Med Chem Lett. 2023 May 15;88:129305. doi: 10.1016/j.bmcl.2023.129305. Epub 2023 Apr 26. PMID: 37116762. 2. Feng LS, Gao C, Liu FW, Wang XP, Zhang ZL. Recent Updates on the Anticancer Activity of Quinoxaline Hybrids (Jan. 2017-Jan. 2022). Curr Top Med Chem. 2022;22(17):1426-1441. doi: 10.2174/1568026622666220428093955. PMID: 36028933. 3. Hu B, Toda K, Wang X, Antczak MI, Smith J, Geboers S, Nishikawa G, Li H, Dawson D, Fink S, Desai AB, Williams NS, Markowitz SD, Ready JM. Orally Bioavailable Quinoxaline Inhibitors of 15-Prostaglandin Dehydrogenase (15-PGDH) Promote Tissue Repair and Regeneration. J Med Chem. 2022 Nov 24;65(22):15327-15343. doi: 10.1021/acs.jmedchem.2c01299. Epub 2022 Nov 2. PMID: 36322935; PMCID: PMC9885488. 4. Chen NY, Lu K, Yuan JM, Li XJ, Gu ZY, Pan CX, Mo DL, Su GF. 3-Arylamino-quinoxaline-2-carboxamides inhibit the PI3K/Akt/mTOR signaling pathways to activate P53 and induce apoptosis. Bioorg Chem. 2021 Sep;114:105101. doi: 10.1016/j.bioorg.2021.105101. Epub 2021 Jun 19. PMID: 34175723.
In vitro protocol:	1. Yang Y, Liu Q, Wang X, Gou S. Design, synthesis, and biological evaluation of novel HDAC inhibitors with a 3-(benzazol-2-yl)quinoxaline framework. Bioorg Med Chem Lett. 2023 May 15;88:129305. doi: 10.1016/j.bmcl.2023.129305. Epub 2023 Apr 26. PMID: 37116762. 2. Feng LS, Gao C, Liu FW, Wang XP, Zhang ZL. Recent Updates on the Anticancer Activity of Quinoxaline Hybrids (Jan. 2017-Jan. 2022). Curr Top Med Chem. 2022;22(17):1426-1441. doi: 10.2174/1568026622666220428093955. PMID: 36028933.
In vivo protocol:	1. Hu B, Toda K, Wang X, Antczak MI, Smith J, Geboers S, Nishikawa G, Li H, Dawson D, Fink S, Desai AB, Williams NS, Markowitz SD, Ready JM. Orally Bioavailable Quinoxaline Inhibitors of 15-Prostaglandin Dehydrogenase (15-PGDH) Promote Tissue Repair and Regeneration. J Med Chem. 2022 Nov 24;65(22):15327-15343. doi: 10.1021/acs.jmedchem.2c01299. Epub 2022 Nov 2. PMID: 36322935; PMCID: PMC9885488. 2. Chen NY, Lu K, Yuan JM, Li XJ, Gu ZY, Pan CX, Mo DL, Su GF. 3-Arylamino-quinoxaline-2-carboxamides inhibit the PI3K/Akt/mTOR signaling pathways to activate P53 and induce apoptosis. Bioorg Chem. 2021 Sep;114:105101. doi: 10.1016/j.bioorg.2021.105101. Epub 2021 Jun 19. PMID: 34175723.

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1: Pinheiro AC, Mendonça Nogueira TC, de Souza MV. Quinoxaline Nucleus: A Promising Scaffold in Anti-cancer Drug Discovery. Anticancer Agents Med Chem. 2016;16(10):1339-52. Review. PubMed PMID: 27349448.

2: Du J, Li XH, Li YJ. Glutamate in peripheral organs: Biology and pharmacology. Eur J Pharmacol. 2016 Aug 5;784:42-8. doi: 10.1016/j.ejphar.2016.05.009. Epub 2016 May 7. Review. PubMed PMID: 27164423.

3: El Newahie AM, Ismail NS, Abou El Ella DA, Abouzid KA. Quinoxaline-Based Scaffolds Targeting Tyrosine Kinases and Their Potential Anticancer Activity. Arch Pharm (Weinheim). 2016 May;349(5):309-26. doi: 10.1002/ardp.201500468. Epub 2016 Apr 9. Review. PubMed PMID: 27062086.

4: Cheng G, Sa W, Cao C, Guo L, Hao H, Liu Z, Wang X, Yuan Z. Quinoxaline 1,4-di-N-Oxides: Biological Activities and Mechanisms of Actions. Front Pharmacol. 2016 Mar 21;7:64. doi: 10.3389/fphar.2016.00064. eCollection 2016. Review. PubMed PMID: 27047380; PubMed Central PMCID: PMC4800186.

5: Unzue A, Lafleur K, Zhao H, Zhou T, Dong J, Kolb P, Liebl J, Zahler S, Caflisch A, Nevado C. Three stories on Eph kinase inhibitors: From in silico discovery to in vivo validation. Eur J Med Chem. 2016 Apr 13;112:347-66. doi: 10.1016/j.ejmech.2016.01.057. Epub 2016 Feb 2. Review. PubMed PMID: 26907157.

6: Tristán-Manzano M, Guirado A, Martínez-Esparza M, Gálvez J, García-Peñarrubia P, Ruiz-Alcaraz AJ. Quinoxalines Potential to Target Pathologies. Curr Med Chem. 2015;22(26):3075-108. Review. PubMed PMID: 26264925.

7: Gerace E, Pellegrini-Giampietro DE, Moroni F, Mannaioni G. Poly(ADP-Ribose)Polymerase 1 (PARP-1) Activation and Ca(2+) Permeable α-Amino-3-Hydroxy-5-Methyl-4-Isoxazolepropionic Acid (AMPA) Channels in Post-Ischemic Brain Damage: New Therapeutic Opportunities? CNS Neurol Disord Drug Targets. 2015;14(5):636-46. Review. PubMed PMID: 25924998.

8: Jampilek J. Recent advances in design of potential quinoxaline anti-infectives. Curr Med Chem. 2014;21(38):4347-73. Review. PubMed PMID: 25312209.

9: Yang Y, Cui M. Radiolabeled bioactive benzoheterocycles for imaging β-amyloid plaques in Alzheimer's disease. Eur J Med Chem. 2014 Nov 24;87:703-21. doi: 10.1016/j.ejmech.2014.10.012. Epub 2014 Oct 7. Review. PubMed PMID: 25305715.

10: Corrêa MF, dos Santos Fernandes JP. Histamine H4 receptor ligands: future applications and state of art. Chem Biol Drug Des. 2015 Apr;85(4):461-80. doi: 10.1111/cbdd.12431. Epub 2014 Oct 27. Review. PubMed PMID: 25228262.

11: Ajani OO. Present status of quinoxaline motifs: excellent pathfinders in therapeutic medicine. Eur J Med Chem. 2014 Oct 6;85:688-715. doi: 10.1016/j.ejmech.2014.08.034. Epub 2014 Aug 10. Review. PubMed PMID: 25128670.

12: Pereira JA, Pessoa AM, Cordeiro MN, Fernandes R, Prudêncio C, Noronha JP, Vieira M. Quinoxaline, its derivatives and applications: A State of the Art review. Eur J Med Chem. 2015 Jun 5;97:664-72. doi: 10.1016/j.ejmech.2014.06.058. Epub 2014 Jul 1. Review. PubMed PMID: 25011559.

13: Nambu A, Tachibana Y. Mechanism of parkinsonian neuronal oscillations in the primate basal ganglia: some considerations based on our recent work. Front Syst Neurosci. 2014 May 23;8:74. doi: 10.3389/fnsys.2014.00074. eCollection 2014. Review. PubMed PMID: 24904309; PubMed Central PMCID: PMC4033056.

14: Moorthy NS, Manivannan E, Karthikeyan C, Trivedi P. 6H-Indolo[2,3-b]quinoxalines: DNA and protein interacting scaffold for pharmacological activities. Mini Rev Med Chem. 2013 Aug;13(10):1415-20. Review. PubMed PMID: 23701655.

15: Jovené C, Chugunova EA, Goumont R. The properties and the use of substituted benzofuroxans in pharmaceutical and medicinal chemistry: a comprehensive review. Mini Rev Med Chem. 2013 Jun 1;13(8):1089-136. Review. PubMed PMID: 23544466.

16: Liu ZY, Sun ZL. The metabolism of carbadox, olaquindox, mequindox, quinocetone and cyadox: an overview. Med Chem. 2013 Dec;9(8):1017-27. Review. PubMed PMID: 23521002.

17: Poulie CB, Bunch L. Heterocycles as nonclassical bioisosteres of α-amino acids. ChemMedChem. 2013 Feb;8(2):205-15. doi: 10.1002/cmdc.201200436. Epub 2013 Jan 15. Review. PubMed PMID: 23322633.

18: González M, Cerecetto H. Quinoxaline derivatives: a patent review (2006--present). Expert Opin Ther Pat. 2012 Nov;22(11):1289-302. doi: 10.1517/13543776.2012.724677. Epub 2012 Sep 13. Review. PubMed PMID: 22971178.

19: Balderas-Renteria I, Gonzalez-Barranco P, Garcia A, Banik BK, Rivera G. Anticancer drug design using scaffolds of β-lactams, sulfonamides, quinoline, quinoxaline and natural products. Drugs advances in clinical trials. Curr Med Chem. 2012;19(26):4377-98. Review. PubMed PMID: 22709002.

20: Shan L. Radioiodinated N-(2-diethylaminoethyl)-6-iodoquinoxaline-2-carboxamide dihydrochloride salt. 2011 Aug 5 [updated 2011 Sep 28]. Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. Available from http://www.ncbi.nlm.nih.gov/books/NBK63869/ PubMed PMID: 21977534.

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