61019-21-4

Basic information

• Product Name: 3-Thiophenecarboxylic acid, 2-amino-5-(4-fluorophenyl)-, ethyl ester
• CAS NO: 61019-21-4
• Molecular Formula: C13H12FNO2S
• Molecular Weight: 265.308
• Mol File: 61019-21-4.mol

Chemical Properties

• CAS DataBase Reference: 3-Thiophenecarboxylic acid, 2-amino-5-(4-fluorophenyl)-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Thiophenecarboxylic acid, 2-amino-5-(4-fluorophenyl)-, ethyl ester(61019-21-4)
• EPA Substance Registry System: 3-Thiophenecarboxylic acid, 2-amino-5-(4-fluorophenyl)-, ethyl ester(61019-21-4)

Safety Data

• Hazardous Substances Data: 61019-21-4(Hazardous Substances Data)

Upstream product

• 1736-67-0 4-fluorophenylacetaldehyde 
• 105-56-6 ethyl 2-cyanoacetate 
• 7589-27-7 2-(4-Fluorophenyl)ethanol 

Downstream Products

• 1217309-77-7 2-amino-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4(3H)-one 
• 1217309-79-9 6-(4-fluorophenyl)-2-phenylthieno[2,3-d]pyrimidin-4(3H)-one 
• 1217309-80-2 ethyl 6-(4-fluorophenyl)-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxylate 
• 1217309-78-8 6-(4-fluorophenyl)-2-methylthieno[2,3-d]pyrimidin-4(3H)-one 
• 1245320-34-6 2-amino-4-N-benzylamino-6-(4-fluorophenyl)thieno[2,3-d]pyrimidine 
• 1217309-83-5 2-(4-chlorophenoxy)-1-(4-(6-(4-fluorophenyl)-2-methylthieno[2,3-d]pyrimidin-4-yl)piperazin-1-yl)ethanone 
• 1217309-88-0 1-(4-(2-amino-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl)-piperazin-1-yl)-2-(4-chlorophenoxy)ethanone 

Relevant articles and documents

Structural modifications at the 6-position of thieno[2,3- d ]pyrimidines and their effects on potency at FLT3 for treatment of acute myeloid leukemia

Fms-like tyrosine kinase 3 (FLT3) is a well-known and important target for the treatment of acute myeloid leukemia (AML). A series of thieno[2,3-d]pyrimidine derivatives from a modification at the 6-position were synthesized to identify effective FLT3 inhibitors. Although compounds 1 and 2 emerged as promising FLT3 inhibitors among the synthesized compounds, both compounds exhibited poor metabolic stability in human and rat liver microsomes. Hence, further optimization was required for the discovery of FLT3 inhibitors, with a focus on improving metabolic stability. Compound 16d, which had structural modifications of the methyl group at the 5-position and the 4-(2-methylaminoethoxy) phenyl group at the 6-position, exhibited good inhibitory activity against FLT3 and showed effective antiproliferative activity against four leukemia cell lines, including MV4-11. Moreover, compound 16d displayed enhanced metabolic stability. The results of this study indicated that 16d could be a promising compound for further optimization and development as a potent FLT3 inhibitor.

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.

Thiophene derivatives

Compounds of the formula: SPC1 Wherein R1 is NHR5 or OR5 where R5 is a hydrogen atom or alkyl group of 1-6 carbon atoms; R2 is a hydrogen atom or a CO.R6 group where R6 is an alk