Vikor Troicki and Pablo Cuevas were the major casualties in the last 16 of the Kremlin Cup on Wednesday.
Serbia's Troicki, seeded three, was beaten 6-2 6-3 by Teymuraz Gabashvili, while fifth seed Cuevas suffered a 6-2 5-7 6-1 defeat against Robin Haase.
But there were no problems for second seed Roberto Bautista Agut as the Spaniard eliminated Turkey's Marsel Ilhan with a 6-2 7-5 victory in just one hour and 15 minutes.
In the first round, Lithuania's Ricardas Berankis saw off Malek Jaziri 6-4 6-4 to set up a meeting against Evgeny Donskoy of Russia.
Uzbekistan's Denis Istomin won 6-3 6-3 against Britain's Aljaz Bedene, securing a second-round match against defending champion and top seed Marin Cilic, while Aslan Karatsev arranged a clash with fourth seed Philipp Kohlschreiber by beating Mikhail Youzhny 6-4 6-4.
France's Lucas Pouille was winning 7-5 4-1 against Simone Bolelli when the Italian retired, and will next face Spain's Daniel Gimeno-Traver in the second round.
Source: PA