41205-31-6Relevant academic research and scientific papers
Synthesis and antitumor activity of thieno-separated tricyclic purines
Seley,Januszczyk,Hagos,Zhang,Dransfield
, p. 4877 - 4883 (2000)
The purine ring system is undoubtedly one of the most ubiquitous heterocyclic ring systems in nature as it has the distinction of being the parent ring in countless derivatives of biological relevance. It is not surprising then that modified purines possess the potential to impact several areas, including a better understanding of the biological effects of DNA damaging agents, enzyme/substrate interactions, and in the development of more potent medicinal agents. One focus for our research at Georgia Tech has centered around the design and synthesis of a series of extended purine analogues containing a heterocyclic spacer ring, with sites set on investigations into their use as (i) potential anticancer and antiviral agents, (ii) dimensional probes for enzyme and coenzyme binding sites, and (iii) structural probes of the minor groove of DNA. The synthesis and preliminary antitumor activity of two thieno-separated purine analogues are described herein. Tricyclic 1 was synthesized in 12 steps from tribromoimidazole and with an overall yield of 7%. Tricyclic 2 was synthesized in 9 steps with an overall yield of 13%. Both 1 and 2 exhibited growth inhibitory effects on HCT116 colorectal cancer cells in vitro.
Use of the vinyl group as an efficient protecting group for azole N- atoms: Synthesis of polyfunctionalized imidazoles and thieno[2,3-d] ? [3,2-d]imidazole
Hartley, David J.,Iddon, Brian
, p. 4647 - 4650 (2007/10/03)
2,4,5-Tribromo-1-vinylimidazole was prepared from 2,4,5-tribromoimidazole and 1,2-dibromoethane and its Br-atoms were replaced regioselectively in the order 2 → 5 → 4 via Br → MgBr and other exchange reactions. Efficient removal of die vinyl groups from die resulting polyfunctionalized imidazoles was achieved with ozone or potassium permanganate. An extension of this methodology has allowed the first synthesis of thieno[2,3-d] ? [3,2-d]-imidazole.
Azoles. Part 4. Nucleophilic Substitution Reactions of Halogenoimidazoles
Iddon, Brian,Khan, Nazir,Lim, Bee Lan
, p. 1437 - 1444 (2007/10/02)
A number of N-protected derivatives of 2,4,5-tribromoimidazole, 4(5)-bromo-5(4)-nitroimidazole, and 2,4(5)-dibromo-5(4)-nitroimidazole have been prepared by standard procedures and treated with various nucleophiles.Whereas 2,4,5-tribromo (and tri-iodo)imidazole reacted with sodium benzenethiolate to give the corresponding 4,5-dihalogenoimidazole and diphenyl disulphide, 1-protected derivatives of 2,4,5-tribromoimidazole reacted with various sodium alkane (or arene)thiolates and with sodium isopropoxide, in isoprpopyl alcohol, by displacement of the 2-bromine atom. 1-Benzyl-5-bromo-4-nitroimidazole (14), 2-(5-bromo-4-nitroimidazol-1-yl)acetate (25), and 5-bromo-4-nitro-1-phenacylimidazole (26) reacted by displacement of the 5-bromine atom.The product arising from reaction of the last compound with ethyl 2-mercaptoacetate in ethanol in the presence of base, cyclised to give ethyl 3-hydroxy-7-nitro-3-phenylimidazolothiazine-2-carboxylate (35).
