By Li-He Zhang, Zhen Xi, Jyoti Chattopadhyaya, Sidney M. Hecht
Whole, up to date assurance of the huge sector of nucleic acid chemistry and biologyAssembling contributions from a set of authors with services in all components of nucleic acids, medicinal chemistry, and healing purposes, Medicinal Chemistry of Nucleic Acids offers an intensive assessment of nucleic acid chemistry—a quickly evolving and hugely difficult self-discipline without delay liable for the advance of antiviral and antitumor medicines. This trustworthy source delves right into a multitude of topic parts related to the research of nucleic acids—such because the new advances in genome sequencing, and the procedures for developing RNA interference (RNAi) dependent drugs—to support pharmaceutical researchers in removal roadblocks that prevent their skill to foretell drug efficacy. delivering the newest state of the art technological know-how during this transforming into box, Medicinal Chemistry of Nucleic Acids includes:In-depth insurance of the advance and alertness of transformed nucleosides and nucleotides in medicinal chemistryA shut examine a wide range of present themes on nucleic acid chemistry and biologyEssential info at the use of nucleic acid medications to regard illnesses like cancerA thorough exploration of siRNA for RNAi and the legislation of microRNA, non-coding RNA (ncRNA), a newly constructing and interesting examine areaThorough in its technique and promising in its message, Medicinal Chemistry of Nucleic Acids probes the recent domain names of pharmaceutical research—and exposes readers to a wealth of latest drug discovery possibilities rising within the dynamic box of nucleic acid chemistry.
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Example text
21 Synthesis of 6 -homoneplanocin A [102]. Reagents and conditions: (a) (i) (TMS)2 NH, BuLi, EtOAc; (ii) LiBH4 ; (iii) TBSCl, Im; (iv) Ac2 O, DMAP, Et3 N; (v) PdCl2 (MeCN)2 , p-benzoquinone; (vi) K2 CO3 ; (b) (i) MsCl, DMAP; (ii) base, NaH, 15crown-5; (c) HCl. 22 Synthesis of fluoroneplanocin A [26]. Reagents and conditions: (a) I2 , CCl4 , Py; (b) (i) NaBH4 , CeCl3 ; (ii) TBDPSCl, Im; (iii) n-BuLi, N -fluorobenzenesulfonimide; (v) TBAF; (c) (i) MsCl, Py; (ii) adenine, K2 CO3 , 18-crown-6; (iii) BBr3 ; (iv) Ac2 O, Py; (v) NH3 /MeOH.
11 Synthesis of 4 -fluorinated carbocyclic nucleoside [64]. Reagents and conditions: (i) adenine (for 93) or 2-amino-6-chloropurine (for 94), Ph3 P, DEAD, THF, rt; (ii) NH3 , MeOH, rt (for 95), 55◦ C (for 100), 100◦ C (for 96 and 102); (iii) DAST, CH2 Cl2 , 0◦ C; (iv) OsO4 , NMO, THF–H2 O, rt; (v) N6 -benzoyladenine (for 99) or 2-amino-6chloropurine (for 100), NaH, (Ph3 P)4 Pd, Ph3 P, DMSO, THF, 55◦ C. 32 μg/mL). Seley-Radtke and coworkers synthesized 5 -deoxy pyrimidine analogues 52 and 53 [78] and evaluated against SAH, but they were inactive.
17 Synthesis of 6-mercaptopurine derivatives [93]. Reagents and Conditions: (a) NaBH4 , MeOH, 0◦ C, 1 h, 96%; (b) (i) MsCl, Et3 N, CH2 Cl2 , 0◦ C, 1 h, 92%; (ii) NaN3 , DMF, 150◦ C, 6 h, 85%; (iii) H2 , 10% Pd/C, MeOH, 30 psi, 2 h; (iv) 5-amino-4,6dichloropyrimidine, Et3 N, n-PrOH, reflux, 24 h, 68% (two steps); (c) CH(OEt)3 , p-TsOH, rt, 14 h, 65%; (d) thiourea, EtOH, reflux, 3 h; (e) TFA/H2 O (2:1, v/v), 50◦ C, 3 h, 52% (two steps); (f) appropriate benzylhalide, NH4 OH/H2 O, rt, 11h. 3 a Host toxicity of uninfected cells was measured by MTT method in at least two independent experiments each of three replica as previously described [15–21].