6-AMINO-1-BUTYL-1H-PYRIMIDINE-2,4-DIONE - CAS 53681-49-5
Catalog number: 53681-49-5
Category: Main Product
Molecular Formula:
C8H13N3O2
Molecular Weight:
183.20772;g/mol
COA:
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Purity:
95%
Synonyms:
6-Amino-1-butyl-1H-pyrimidine-2,4-dione;53681-49-5;ZINC03313203;1-butyl-6-aminouracil;AC1M6RMS;AC1Q2WWM
MSDS:
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Density:
1.174g/cm3
InChIKey:
MKBLKULBTBPLRX-UHFFFAOYSA-N
InChI:
InChI=1S/C8H13N3O2/c1-2-3-4-11-6(9)5-7(12)10-8(11)13/h5H,2-4,9H2,1H3,(H,10,12,13)
Canonical SMILES:
CCCCN1C(=CC(=O)NC1=O)N
1.One-pot synthesis and in-vitro anticancer evaluation of 5-(2'-indolyl)thiazoles.
Vaddula BR1, Tantak MP2, Sadana R3, Gonzalez MA1, Kumar D2. Sci Rep. 2016 Mar 29;6:23401. doi: 10.1038/srep23401.
A series of 5-(2'-indolyl)thiazoles were synthesized and evaluated for their cytotoxicity against selected human cancer cell lines. The reaction of thioamides 3 with 3-tosyloxypentane-2,4-dione 4 led to in situ formation of 5-acetylthiazole 5 which upon treatment with arylhydrazines 6 in polyphosphoric acid resulted in the formation of 5-(2'-indolyl)thiazoles 2. Among the synthesized 5-(2'-indolyl)thiazoles, compounds 2d-f, and 2h exhibited encouraging anticancer activity and also selectivity towards particular cell lines (IC50 = 10-30 μM). Further studies on the SAR of compound 2e may result in good anticancer activity.
2.Two novel phenanthraquinones with anti-cancer activity isolated from Bletilla striata.
Sun A1, Liu J2, Pang S1, Lin J2, Xu R3. Bioorg Med Chem Lett. 2016 May 1;26(9):2375-9. doi: 10.1016/j.bmcl.2016.01.076. Epub 2016 Jan 29.
7-Hydroxy-2-methoxy-phenanthrene-3,4-dione and 3',7',7-trihydroxy-2,2',4'-trimethoxy-[1,8'-biphenanthrene]-3,4-dione, two novel compounds and four known compounds were isolated from Bletilla striata. The structures of the compounds were established on the basis of extensive spectroscopic analysis. The two compounds exhibited antiproliferative effects using the MTT test; these effects may be due to cell cycle arrest and inducing ROS generation.
3.Crystal structures of (S)-(+)-5-(3-bromo/chloro-4-isopropoxyphen-yl)-5-methyl-imidazolidine-2,4-dione.
Ohba S1, Koura M2, Sumida H2, Shibuya K2. Acta Crystallogr E Crystallogr Commun. 2016 Jan 16;72(Pt 2):184-7. doi: 10.1107/S2056989015023014. eCollection 2016.
In (S)-(+)-5-(3-bromo-4-isopropoxyphen-yl)-5-methyl-imidazolidine-2,4-dione, C13H15BrN2O3, (I), the hydantoin groups are connected via inter-molecular N-H⋯O hydrogen bonds, forming a terraced sheet structure. In the chloro analogue, (S)-(+)-5-(3-chloro-4-isopropoxyphen-yl)-5-methyl-imidazolidine-2,4-dione, C13H15ClN2O3, (II), the inter-molecular N-H⋯O hydrogen-bonding network forms a flat sheet. Comparison of the crystal structures reveals that (II) is more loosely packed than (I).
4.Human 3α-hydroxysteroid dehydrogenase type 3: structural clues of 5α-DHT reverse binding and enzyme down-regulation decreasing MCF7 cell growth.
Zhang B1, Hu XJ2, Wang XQ3, Thériault JF3, Zhu DW3, Shang P4, Labrie F3, Lin SX5. Biochem J. 2016 Apr 15;473(8):1037-46. doi: 10.1042/BCJ20160083. Epub 2016 Feb 29.
Human 3α-HSD3 (3α-hydroxysteroid dehydrogenase type 3) plays an essential role in the inactivation of the most potent androgen 5α-DHT (5α-dihydrotestosterone). The present study attempts to obtain the important structure of 3α-HSD3 in complex with 5α-DHT and to investigate the role of 3α-HSD3 in breast cancer cells. We report the crystal structure of human 3α-HSD3·NADP(+)·A-dione (5α-androstane-3,17-dione)/epi-ADT (epiandrosterone) complex, which was obtained by co-crystallization with 5α-DHT in the presence of NADP(+) Although 5α-DHT was introduced during the crystallization, oxidoreduction of 5α-DHT occurred. The locations of A-dione and epi-ADT were identified in the steroid-binding sites of two 3α-HSD3 molecules per crystal asymmetric unit. An overlay showed that A-dione and epi-ADT were oriented upside-down and flipped relative to each other, providing structural clues for 5α-DHT reverse binding in the enzyme with the generation of different products.
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CAS 53681-49-5 6-AMINO-1-BUTYL-1H-PYRIMIDINE-2,4-DIONE

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