Flavonoide-type compounds bearing an o-rhamnosyl residue

A compound of the following Formula (II) or a solvate thereof

• wherein:
• is a double bond or a single bond;
• R1 and R2 are independently selected from hydrogen, C1-5 alkyl, C2-5 alkenyl, C2-5 alkynyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, —Ra—Rb, —Ra—ORb, —Ra—ORd, —Ra—ORa—ORb, —Ra—ORa—ORd, —Ra—SRb, —Ra—SRa—SRb, —Ra—NRbRb, —Ra-halogen, —Ra—(C1-5 haloalkyl), —Ra—CN, —Ra—CO—Rb, —Ra—CO—O—Rb, —Ra—O—CO—Rb, —Ra—CO—NRbRb, —Ra—NRb—CO—Rb, —Ra—SO2—NRbRb and —Ra—NRb—SO2—Rb;
• wherein said alkyl, said alkenyl, said alkynyl, said heteroalkyl, said cycloalkyl, said heterocycloalkyl, said aryl and said heteroaryl are each optionally substituted with one or more groups Rc;
• wherein R2 is different from —OH;
• or R1 and R2 are joined together to form, together with the carbon atom(s) that they are attached to, a carbocyclic or heterocyclic ring being optionally substituted with one or more substituents Re;
• wherein each Re is independently selected from C1-5 alkyl, C2-5 alkenyl, C2-5 alkynyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, —Ra—Rb, —Ra—ORb, —Ra—ORd, —Ra—ORa—ORb, —Ra—ORa—ORd, —Ra—SRb, —Ra—SRa—SRb, —Ra—NRbRb, —Ra-halogen, —Ra—(C1-5 haloalkyl), —Ra—CN, —Ra—CO—Rb, —Ra—CO—O—Rb, —Ra—O—CO—Rb, —Ra—CO—NRbRb, —Ra—NRb—CO—Rb, —Ra—SO2—NRbRb and —Ra—NRb—SO2—Rb;
• wherein said alkyl, said alkenyl, said alkynyl, said heteroalkyl, said cycloalkyl, said heterocycloalkyl, said aryl and said heteroaryl are each optionally substituted with one or more groups Rc;
• R4, R5 and R6 are independently selected from hydrogen, C1-5 alkyl, C2-5 alkenyl, C2-5 alkynyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, —Ra—Rb, —Ra—ORb, —Ra—ORd, —Ra—ORa—ORb, —Ra—ORa—ORd, —Ra—SRb, —Ra—SRa—SRb, —Ra—NRbRb, —Ra-halogen, —Ra—(C1-5 haloalkyl), —Ra—CN, —Ra—CO—Rb, —Ra—CO—O—Rb, —Ra—O—CO—Rb, —Ra—CO—NRbRb, —Ra—NRb—CO—Rb, —Ra—SO2—NRbRb and —Ra—NRb—SO2—Rb;
• wherein said alkyl, said alkenyl, said alkynyl, said heteroalkyl, said cycloalkyl, said heterocycloalkyl, said aryl and said heteroaryl are each optionally substituted with one or more groups Rc;
• or alternatively, R4 is selected from hydrogen, C1-5 alkyl, C2-5 alkenyl, C2-5 alkynyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, —Ra—Rb, —Ra—ORb, —Ra—ORd, —Ra—ORa—ORb, —Ra—ORa—ORd, —Ra—SRb, —Ra—SRa—SRb, —Ra—NRbRb, —Ra-halogen, —Ra—(C1-5 haloalkyl), —Ra—CN, —Ra—CO—Rb, —Ra—CO—O—Rb, —Ra—O—CO—Rb, —Ra—CO—NRbRb, —Ra—NRb—CO—Rb, —Ra—SO2—NRbRb and —Ra—NRb—SO2—Rb;
• wherein said alkyl, said alkenyl, said alkynyl, said heteroalkyl, said cycloalkyl, said heterocycloalkyl, said aryl and said heteroaryl are each optionally substituted with one or more groups Rc;
• and
• R5 and R6 are joined together to form, together with the carbon atoms that they are attached to, a carbocyclic or heterocyclic ring being optionally substituted with one or more substituents Rc;
• or alternatively, R4 and R5 are joined together to form, together with the carbon atoms that they are attached to, a carbocyclic or heterocyclic ring being optionally substituted with one or more substituents Rc;
• and
• R6 is selected from hydrogen, C1-5 alkyl, C2-5 alkenyl, C2-5 alkynyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, —Ra—Rb, —Ra—ORb, —Ra—ORd, —Ra—ORa—ORb, —Ra—ORa—ORd, —Ra—SRb, —Ra—SRa—SRb, —Ra—NRbRb, —Ra-halogen, —Ra—(C1-5 haloalkyl), —Ra—CN, —Ra—CO—Rb, —Ra—CO—O—Rb, —Ra—O—CO—Rb, —Ra—CO—NRbRb, —Ra—NRb—CO—Rb, —Ra—SO2—NRbRb and —Ra—NRb—SO2—Rb;
• wherein said alkyl, said alkenyl, said alkynyl, said heteroalkyl, said cycloalkyl, said heterocycloalkyl, said aryl and said heteroaryl are each optionally substituted with one or more groups Rc;
• each Ra is independently selected from a single bond, (C1-5 alkylene, C2-5 alkenylene, arylene and heteroarylene;
• wherein said alkylene, said alkenylene, said arylene and said heteroarylene are each optionally substituted with one or more groups Rc;
• each Rb is independently selected from hydrogen, C1-5 alkyl, C2-5 alkenyl, C2-5 alkynyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl and heteroaryl;
• wherein said alkyl, said alkenyl, said alkynyl, said heteroalkyl, said cycloalkyl, said heterocycloalkyl, said aryl and said heteroaryl are each optionally substituted with one or more groups Rc;
• each Rc is independently selected from C1-5 alkyl, C2-5 alkenyl, C2-5 alkynyl, —(C0-3 alkylene)-OH, —(C0-3 alkylene)-O—Rd, —(C0-3 alkylene)-O((C1-5 alkyl), —(C0-3 alkylene)-O-aryl, —(C0-3 alkylene)-O(C1-5 alkylene)-OH, —(C0-3 alkylene)-O(C1-5 alkylene)-O—Rd, —(C0-3 alkylene)-O(C1-5 alkylene)-O(C1-5 alkyl), —(C0-3 alkylene)-SH, —(C0-3 alkylene)-S(C1-5 alkyl), —(C0-3 alkylene)-S-aryl, —(C0-3 alkylene)-S(C1-5 alkylene)-SH, —(C0-3 alkylene)-S(C1-5 alkylene)-S(C1-5 alkyl), —(C0-3 alkylene)-NH2, —(C0-3 alkylene)-NH(C1-5 alkyl), —(C0-3 alkylene)-N(C1-5 alkyl)(C1-5 alkyl), —(C0-3 alkylene)-halogen, —(C0-3 alkylene)-(C1-5 haloalkyl), —(C0-3 alkylene)-CN, —(C0-3 alkylene)-CHO, —(C0-3 alkylene)-CO—(C1-5 alkyl), —(C0-3 alkylene)-COOH, —(C0-3 alkylene)-CO—O—(C1-5 alkyl), —(C0-3 alkylene)-O—CO—(C1-5 alkyl), —(C0-3 alkylene)-CO—NH2, —(C0-3 alkylene)-CO—NH(C1-5 alkyl), —(C0-3 alkylene)-CO—N(C1-5 alkyl)(C1-5 alkyl), —(C0-3 alkylene)-NH—CO—(C1-5 alkyl), —(C0-3 alkylene)-N(C1-5 alkyl)-CO—(C1-5 alkyl), —(C0-3 alkylene)-SO2—NH2, —(C0-3 alkylene)-SO2—NH(C1-5 alkyl), —(C0-3 alkylene)-SO2—N(C1-5 alkyl)(C1-5 alkyl), —(C0-3 alkylene)-NH—SO2—(C1-5 alkyl), and —(C0-3 alkylene)-N(C1-5 alkyl)-SO2—(C1-5 alkyl);
• wherein said alkyl, said alkenyl, said alkynyl and the alkyl or alkylene moieties comprised in any of the aforementioned groups Rc are each optionally substituted with one or more groups independently selected from halogen, —CF3, —CN, —OH, —O—Rd, —O—C1-4 alkyl and —S—C1-4 alkyl;
• R3 is —O-(rhamnosyl) wherein said rhamnosyl is optionally substituted at one or more of its —OH groups with one or more groups independently selected from C1-5 alkyl, C2-5 alkenyl, C2-5 alkynyl, a monosaccharide, a disaccharide and an oligosaccharide;
• and
• wherein each Rd is independently selected from a monosaccharide, a disaccharide and an oligosaccharide;
• with the proviso that, if R4 is hydrogen, R5 is —OH and is a double bond, then R1 is not methyl.