1217309-77-7

Basic information

• Product Name: 2-amino-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4(3H)-one
• Synonyms: 2-amino-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4(3H)-one
• CAS NO: 1217309-77-7
• Molecular Weight: 261.279
• Mol File: 1217309-77-7.mol

Chemical Properties

• CAS DataBase Reference: 2-amino-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4(3H)-one(1217309-77-7)
• EPA Substance Registry System: 2-amino-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4(3H)-one(1217309-77-7)

Safety Data

• Hazardous Substances Data: 1217309-77-7(Hazardous Substances Data)

Upstream product

• 61019-21-4 ethyl 2-amino-5-(4-fluorophenyl)lthiophene-3-carboxylate 
• 29671-92-9 chloroformamidine hydrochloride 
• 1736-67-0 4-fluorophenylacetaldehyde 
• 7589-27-7 2-(4-Fluorophenyl)ethanol 

Downstream Products

• 1217309-81-3 2-amino-4-N-piperazinyl-6-(4-fluorophenyl)-thieno[2,3-d]pyrimidine 
• 1245320-51-7 4-ethoxy-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-2-amine 
• 1245320-34-6 2-amino-4-N-benzylamino-6-(4-fluorophenyl)thieno[2,3-d]pyrimidine 

Relevant articles and documents

ANTI-CANCER ACTIVITY OF NOVEL BICYCLIC HETEROCYCLES

The present invention relates to compound of formula I, II, III, or IV, and/or a pharmaceutical acceptable addition salt thereof and/or a stereoisomer thereof and/or a solvate thereof, Formulas (I), (II), (III) and (IV) wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R11, and R12 are as defined in the claim 1 or as described in detail in the description of the invention, and to the use of said compounds to treat or prevent proliferative disorders and their use to manufacture a medicine to treat or prevent proliferative disorders, particularly cancer such as leukemia. The present invention also relates to pharmaceutical compositions of said compounds and the use of said pharmaceutical compositions to treat or prevent proliferative disorders. The present invention further relates to the use of said compounds as biologically active ingredients, more specifically as medicaments for the treatment of proliferative disorders and pathologic conditions such as, but not limited to, cancer such as leukemia.

Antiviral Activity of Novel Bicyclic Heterocycles

The present invention relates to compound of Formula I, II, III, or IV, and/or a pharmaceutical acceptable addition salt thereof and/or a stereoisomer thereof and/or a solvate thereof, wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R11, and R12 are as defined in the claim 1 or as described in detail in the description of the invention, and to the use of said compounds to treat or prevent viral infections and their use to manufacture a medicine to treat or prevent viral infections, particularly infections with RNA-viruses belonging to the family of the Retroviridae, the family of the Flaviviridae and the family of the Picornaviridae and more preferably infections with Human Immunodeficiency Virus 1 (HIV1), Human Immunodeficiency Virus 2 (HIV2), Hepatitis C virus (HCV), Dengue virus, and enteroviruses like Coxsackievirus, Rhinovirus and Poliovirus. The present invention also relates to pharmaceutical compositions of said compounds and the use of said pharmaceutical compositions to treat or prevent viral infections. The present invention further relates to the use of said compounds as biologically active ingredients, more specifically as medicaments for the treatment of viral disorders and pathologic conditions such as, but not limited to, viral infections with Human Immunodeficiency Virus 1 (HIV1), Human Immunodeficiency Virus 2 (HIV2), Hepatitis C virus (HCV), Dengue virus, and enteroviruses like Coxsackievirus, Rhinovirus and Poliovirus.

THIAZOLOPYRIMIDINE MODULATORS AS IMMUNOSUPPRESSIVE AGENTS

The present invention relates to compound of formula I, II, III, or IV, and/or a pharmaceutical acceptable addition salt thereof and/or a stereoisomer thereof and/or a solvate thereof, wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R11, and R12 are as defined in the claim 1. The present invention also relates to a method for their preparation, as well as to pharmaceutical compositions thereof. The present invention further relates to the use of said compounds as biologically active ingredients, more specifically as medicaments for the treatment of disorders and pathologic conditions such as, but not limited to, immune and auto-immune disorders, organ and cells transplant rejections.

Discovery of 7- N -piperazinylthiazolo[5,4- d ]pyrimidine analogues as a novel class of immunosuppressive agents with in vivo biological activity

Herein we describe the synthesis and in vitro and in vivo activity of thiazolo[5,4-d]pyrimidines as a novel class of immunosuppressive agents, useful for preventing graft rejection after organ transplantation. This research resulted in the discovery of a series of compounds with potent activity in the mixed lymphocyte reaction (MLR) assay, which is well-known as the in vitro model for in vivo rejection after organ transplantation. The most potent congeners displayed IC50 values of less than 50 nM in this MLR assay and hence are equipotent to cyclosporin A, a clinically used immunosuppressive drug. One representative of this series was further evaluated in a preclinical animal model of organ transplantation and showed excellent in vivo efficacy. It validates these compounds as new promising immunosuppressive drugs.

Synthesis, immunosuppressive activity and structure-activity relationship study of a new series of 4-N-piperazinyl-thieno[2,3-d]pyrimidine analogues

The synthesis of a new series of 4-N-piperazinyl-thieno[2,3-d]pyrimidines is described. The synthetic route allows introducing structural variety at positions 2, 4 and 6 of the scaffold. Evaluation of their immunosuppressive activity in a Mixed Lymphocyte Reaction (MLR) assay revealed that the most potent compound has an IC50-value of 66 nM and therefore deserves attention for further medicinal chemistry optimization.