| Identification | Back Directory | [Name]
Mirin | [CAS]
1198097-97-0 | [Synonyms]
CS-2593
(Z)-2-Amino-5-(4-hydroxybenzylidene)thiazol-4(5H)-one
(5Z)-2-Amino-5-[(4-hydroxyphenyl)methylene]-4(5H)-thiazolone
4(5H)-Thiazolone, 2-amino-5-[(4-hydroxyphenyl)methylene]-, (5Z)- | [Molecular Formula]
C10H8N2O2S | [MDL Number]
MFCD05885480 | [MOL File]
1198097-97-0.mol | [Molecular Weight]
220.25 |
| Chemical Properties | Back Directory | [Boiling point ]
441.6±55.0 °C(Predicted) | [density ]
1.49±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
insoluble in EtOH; insoluble in H2O; ≥9.3 mg/mL in DMSO | [form ]
solid | [pka]
8.70±0.30(Predicted) | [color ]
Light yellow to yellow |
| Hazard Information | Back Directory | [Uses]
Mirin is an MRN-ATM pathway inhibitor blocking 3’ and 5’ exonuclease activity associated with Mre11, inducing G2 cell cycle arrest. | [Biological Activity]
mirin is a potent mrn complex inhibitor. mirin inhibits mre11-associated exonuclease activity, rather than alters dna-binding or mrn complex formation. moreover, mirin prevents mrn-dependent activation of atm in response to dna double-strand breaks, with an ic50 value of 12 μm. the mrn complex acts as a dna damage sensor, responsible for maintaining genome stability during dna replication, promoting homology-dependent dna repair and activating atm. the mrn-atm pathway plays an essential role in sensing and signaling from dna double-strand breaks.1. dupré a, boyer-chatenet l, sattler rm, et al. a forward chemical genetic screen reveals an inhibitor of the mre11-rad50-nbs1 complex. nature chemical biology, 2008, 4(2): 119-125. | [Synthesis]
GENERAL METHODS: (Z)-2-Amino-5-(4-hydroxybenzylidene)thiazol-4(5H)-one was synthesized from p-hydroxybenzaldehyde and pseudothioglycolide. The procedure was as follows: a mixture of p-hydroxybenzaldehyde (300 mg), pseudothioglycolide (1.1 eq.) and sodium acetate (3.0 eq.) was heated and refluxed for 3 to 7 hours under acetic acid (4 mL/1 g sodium acetate) as a solvent. Upon completion of the reaction, the reaction mixture was cooled and water was added to precipitate the product. The precipitate was collected by filtration and washed with water, dichloromethane and/or ethyl acetate depending on the physical properties of the starting material to finalize the target product. The product was an orange solid with a reaction time of 3 hours, a yield of 61.8% and a melting point of over 300 °C. The structure of the product was determined by 1H NMR (500 MHz, DMSO-d6) δ 10.10 (s, 1H), 9.29 (brs, 1H), 9.04 (s, 1H), 7.49 (s, 1H), 7.40 (d, 2H, J = 9.0 Hz), 6.88 (d, 2H, J = 8.5Hz); 13C NMR (100 MHz, DMSO-d6) δ 181.4, 176.1, 159.6, 132.1, 130.2, 126.0, 125.5, 116.8; and mass spectrometry (ESI) m/z 219 ([M-H]-) were confirmed. | [storage]
Store at +4°C | [References]
[1] Journal of Medicinal Chemistry, 2010, vol. 53, # 1, p. 273 - 281
[2] Patent: US2014/23603, 2014, A1. Location in patent: Paragraph 0268; 0271
[3] Patent: KR101677122, 2016, B1. Location in patent: Paragraph 0411-0412; 0417
[4] Bioscience, Biotechnology and Biochemistry, 2018, vol. 82, # 5, p. 759 - 767
[5] Synthetic Communications, 2013, vol. 43, # 7, p. 961 - 978 |
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