TUN53037 | CAS#553-03-7 | Bioactive building block

MedKoo Cat#: 463169 | Name: TUN53037

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Description:

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

TUN53037, also known as 3,4-Dihydroquinolin-2(1H)-one is a building block. It has been used in the synthesis of compounds with antidepressant and anticonvulsant activities, as well as dual ligands of sigma (σ) receptors and the NMDA receptor GluN2b subunit that have antioxidant and neuroprotective properties. This product has no formal name at the moment. For the convenience of communication, a temporary code name was therefore proposed according to MedKoo Chemical Nomenclature (see web page: https://www.medkoo.com/page/naming).

Chemical Structure

TUN53037

CAS#553-03-7

Theoretical Analysis

MedKoo Cat#: 463169

Name: TUN53037

CAS#: 553-03-7

Chemical Formula: C9H9NO

Exact Mass: 147.0684

Molecular Weight: 147.18

Elemental Analysis: C, 73.45; H, 6.16; N, 9.52; O, 10.87

Price and Availability

Size	Price	Availability	Quantity
5g	USD 550.00	2 Weeks
10g	USD 950.00	2 Weeks

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Related CAS #

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Synonym

3,4-Dihydroquinolin-2(1H)-one; 3,4 Dihydroquinolin 2(1H) one; TUN53037; TUN-53037; TUN 53037

IUPAC/Chemical Name

3,4-dihydroquinolin-2(1H)-one

InChi Key

TZOYXRMEFDYWDQ-UHFFFAOYSA-N

InChi Code

InChI=1S/C9H9NO/c11-9-6-5-7-3-1-2-4-8(7)10-9/h1-4H,5-6H2,(H,10,11)

SMILES Code

O=C1NC2=C(C=CC=C2)CC1

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 147.18 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: Wang S, Liu H, Lei K, Li G, Li J, Wei Y, Wang X, Liu R. Synthesis of 3,4-dihydroquinolin-2(1H)-one derivatives with anticonvulsant activity and their binding to the GABAA receptor. Bioorg Chem. 2020 Oct;103:104182. doi: 10.1016/j.bioorg.2020.104182. Epub 2020 Aug 27. PMID: 32890992. 2: Wang S, Liu H, Wang X, Lei K, Li G, Li J, Liu R, Quan Z. Synthesis of 1,3,4-oxadiazole derivatives with anticonvulsant activity and their binding to the GABAA receptor. Eur J Med Chem. 2020 Nov 15;206:112672. doi: 10.1016/j.ejmech.2020.112672. Epub 2020 Aug 6. PMID: 32798790. 3: Son J, Lee SY. Small molecule DTDQ exerts anti-metastatic effects in DU145 human castration-resistant prostate cancer cells via modulations of ERK, JNK, p38 and c-Myc signaling pathways. Bioorg Med Chem Lett. 2020 Jul 1;30(13):127223. doi: 10.1016/j.bmcl.2020.127223. Epub 2020 Apr 27. PMID: 32371099. 4: Küçükbay H, Gönül Z, Küçükbay FZ, Angeli A, Bartolucci G, Supuran CT. Preparation, carbonic anhydrase enzyme inhibition and antioxidant activity of novel 7-amino-3,4-dihydroquinolin-2(1H)-one derivatives incorporating mono or dipeptide moiety. J Enzyme Inhib Med Chem. 2020 Dec;35(1):1021-1026. doi: 10.1080/14756366.2020.1751620. PMID: 32297533; PMCID: PMC7178833. 5: Ogino M, Fedorov Y, Adams DJ, Okada K, Ito N, Sugiyama M, Ogino T. Vesiculopolins, a New Class of Anti-Vesiculoviral Compounds, Inhibit Transcription Initiation of Vesiculoviruses. Viruses. 2019 Sep 14;11(9):856. doi: 10.3390/v11090856. PMID: 31540123; PMCID: PMC6783830. 6: Ji Q, Deng Q, Li B, Li B, Shen Y. Design, synthesis and biological evaluation of novel 5-(piperazin-1-yl)quinolin-2(1H)-one derivatives as potential chitin synthase inhibitors and antifungal agents. Eur J Med Chem. 2019 Oct 15;180:204-212. doi: 10.1016/j.ejmech.2019.07.035. Epub 2019 Jul 10. PMID: 31306907. 7: Chen W, Sun C, Zhang Y, Hu T, Zhu F, Jiang X, Abame MA, Yang F, Suo J, Shi J, Shen J, Aisa HA. Oxidative Aromatization of 3,4-Dihydroquinolin-2(1 H)-ones to Quinolin-2(1 H)-ones Using Transition-Metal-Activated Persulfate Salts. J Org Chem. 2019 Jul 5;84(13):8702-8709. doi: 10.1021/acs.joc.9b00756. Epub 2019 Jun 17. PMID: 31244162. 8: Bozdag M, Bua S, Osman SM, AlOthman Z, Supuran CT. Carbonic anhydrase I, II, IV and IX inhibition with a series of 7-amino-3,4-dihydroquinolin-2(1H)-one derivatives. J Enzyme Inhib Med Chem. 2017 Dec;32(1):885-892. doi: 10.1080/14756366.2017.1337759. PMID: 28644059; PMCID: PMC6445181. 9: Park S, Lee J, Lee SY. IDH-Inhibiting Small Molecule DTDQ Inhibits Migration and Invasion of A549 Human Non-Small-Cell Lung Cancer Cells via Sequential Inactivation Of ERK and P38 Signaling Pathways. Cell Biochem Biophys. 2018 Jun;76(1-2):255-263. doi: 10.1007/s12013-017-0789-2. Epub 2017 Mar 21. PMID: 28321613. 10: Hanyu M, Kawamura K, Takei M, Furutsuka K, Shiomi S, Fujishiro T, Ogawa M, Nengaki N, Hashimoto H, Fukumura T, Zhang MR. Radiosynthesis and quality control of [11C]TASP457 as a clinically useful PET ligand for imaging of histamine H3 receptors in human brain. Nucl Med Biol. 2016 Nov;43(11):679-684. doi: 10.1016/j.nucmedbio.2016.08.004. Epub 2016 Aug 10. PMID: 27580212. 11: Prus AJ, Wise LE, Pehrson AL, Philibin SD, Bang-Andersen B, Arnt J, Porter JH. Discriminative stimulus properties of 1.25mg/kg clozapine in rats: Mediation by serotonin 5-HT2 and dopamine D4 receptors. Brain Res. 2016 Oct 1;1648(Pt A):298-305. doi: 10.1016/j.brainres.2016.08.004. Epub 2016 Aug 5. PMID: 27502027. 12: Li Y, Wang F, Zhang PZ, Yang M. [Chemical Constituents from Periplaneta americana]. Zhong Yao Cai. 2015 Oct;38(10):2038-41. Chinese. PMID: 27254913. 13: Wang AF, Zhu YL, Wang SL, Hao WJ, Li G, Tu SJ, Jiang B. Metal-Free Radical Haloazidation of Benzene-Tethered 1,7-Enynes Leading to Polyfunctionalized 3,4-Dihydroquinolin-2(1H)-ones. J Org Chem. 2016 Feb 5;81(3):1099-105. doi: 10.1021/acs.joc.5b02655. Epub 2016 Jan 7. PMID: 26716579. 14: Shao CL, Xu RF, Wang CY, Qian PY, Wang KL, Wei MY. Potent Antifouling Marine Dihydroquinolin-2(1H)-one-Containing Alkaloids from the Gorgonian Coral-Derived Fungus Scopulariopsis sp. Mar Biotechnol (NY). 2015 Aug;17(4):408-15. doi: 10.1007/s10126-015-9628-x. Epub 2015 Apr 2. PMID: 25833409. 15: Kołaczkowski M, Marcinkowska M, Bucki A, Śniecikowska J, Pawłowski M, Kazek G, Siwek A, Jastrzębska-Więsek M, Partyka A, Wasik A, Wesołowska A, Mierzejewski P, Bienkowski P. Novel 5-HT6 receptor antagonists/D2 receptor partial agonists targeting behavioral and psychological symptoms of dementia. Eur J Med Chem. 2015 Mar 6;92:221-35. doi: 10.1016/j.ejmech.2014.12.045. Epub 2014 Dec 24. PMID: 25557493. 16: Mai WP, Sun GC, Wang JT, Song G, Mao P, Yang LR, Yuan JW, Xiao YM, Qu LB. Silver-catalyzed radical tandem cyclization: an approach to direct synthesis of 3-acyl-4-arylquinolin-2(1H)-ones. J Org Chem. 2014 Sep 5;79(17):8094-102. doi: 10.1021/jo501301t. Epub 2014 Aug 7. PMID: 25084243. 17: Luoni A, Fumagalli F, Racagni G, Riva MA. Repeated aripiprazole treatment regulates Bdnf, Arc and Npas4 expression under basal condition as well as after an acute swim stress in the rat brain. Pharmacol Res. 2014 Feb;80:1-8. doi: 10.1016/j.phrs.2013.11.008. Epub 2013 Dec 2. PMID: 24309096. 18: Smith AL, Freeman SM, Voll RJ, Young LJ, Goodman MM. Investigation of an F-18 oxytocin receptor selective ligand via PET imaging. Bioorg Med Chem Lett. 2013 Oct 1;23(19):5415-20. doi: 10.1016/j.bmcl.2013.07.045. Epub 2013 Jul 30. PMID: 23978650; PMCID: PMC3955700. 19: Luedtke RR, Mishra Y, Wang Q, Griffin SA, Bell-Horner C, Taylor M, Vangveravong S, Dillon GH, Huang RQ, Reichert DE, Mach RH. Comparison of the binding and functional properties of two structurally different D2 dopamine receptor subtype selective compounds. ACS Chem Neurosci. 2012 Dec 19;3(12):1050-62. doi: 10.1021/cn300142q. Epub 2012 Oct 12. PMID: 23259040; PMCID: PMC3526968. 20: Chen IL, Chen JJ, Lin YC, Peng CT, Juang SH, Wang TC. Synthesis and antiproliferative activities of N-(naphthalen-2-yl)acetamide and N-(substituted phenyl)acetamide bearing quinolin-2(1H)-one and 3,4-dihydroquinolin-2(1H)-one derivatives. Eur J Med Chem. 2013 Jan;59:227-34. doi: 10.1016/j.ejmech.2012.11.016. Epub 2012 Nov 20. PMID: 23229058.

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DC-05