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string str="/Tools/Leaveword.shtml
/Tools/OK.shtml
/ABC/xxxxxx.shtml,ttryrt,/ABC/xxxxxx-m-2.shtml
/CDE/xxxxxxx.shtml,";
str=Regex.Replace(str,"(?is)(?<=/[a-z]{1,}\.)shtml","html");
string str=@"/Tools/Leaveword.shtml
/Tools/OK.shtml
/ABC/xxxxxx.shtml,ttryrt,/ABC/xxxxxx-m-2.shtml
/CDE/xxxxxxx.shtml,";
str = Regex.Replace(str, @"(?i)(?<=/(?:(?![^.\s]*?(?:Leaveword|OK|-m-2))[^.]+?)\.)shtml", "html");
/*
/Tools/Leaveword.shtml
/Tools/OK.shtml
/ABC/xxxxxx.html,ttryrt,/ABC/xxxxxx-m-2.shtml
/CDE/xxxxxxx.html,
*/