Design, Synthesis, and Analysis of Minor Groove Binder Pyrrolepolyamide-𝟐^′-Deoxyguanosine Hybrids

Scheme 1

Reaction conditions (i) CL₃CCOCL, Et₂O, rt, 1 hour. (ii) HNO₃, Ac₂O, −10°C ∼ rt, 1 hour. (iii) NaOMe, MeOH, rt, 15 minutes. (iv) 1. H₂, 10% Pd/C, AcOEt, rt, 12 hours; 2. (Boc)₂O, Et₂O, rt, 2 hours. (v) 1. 1 M NaOH, H₂O/MeOH, 60°C, 1 ∼ 2 hours; 2. 10% HCL aq. (vi) 1. H₂, 10% Pd/C, AcOEt, rt, 12 hours; 2. 6, EDCI, DMAP, DMF, rt, 3 hours. (vii) 1. AcCL, MeOH, 0°C, 30 minutes. 2. 6, EDCI, DMAP, DMF, rt, 3 hours. (viii) 1. AcCL, MeOH, 0°C, 30 minutes; 2. HCOOH, CDI, THF, −40°C, 30 minutes. (ix) ethyl 𝛽-alanine, EDCI, DMAP, DMF, rt, 3 hours.