89639-37-2

Usage

InChI:InChI=1/C6H7ClN2OS/c1-11-6-8-4(3-7)2-5(10)9-6/h2H,3H2,1H3,(H,8,9,10)

Upstream product

• 638-07-3 ethyl (2-chloroaceto)acetate 
• 14527-26-5 2-methylisothiourea sulphate 
• 867-44-7 S-Methylisothiourea sulfate 
• 41658-12-2 Chlortetrolsaeuremethylester 
• 53114-57-1 S-methylisothiourea hydrochloride 
• 147895-43-0 S-methylisothiourea hemisulphate 
• 2986-19-8 carbamimidothioic acid methyl ester 

Downstream Products

• 94694-53-8 4-chloro-6-(chloromethyl)-2-(methylthio)pyrimidine 
• 18592-13-7 6-chloromethyluracil 
• 944058-84-8 6-(benzenesulfonylmethyl)-2-methylsulfanyl-pyrimidin-4-ol 

Relevant academic research and scientific papers

Design, Synthesis, and Characterization of Novel CXCR4 Antagonists Featuring Cyclic Amines

Chemokine receptor CXCR4 and its natural ligand CXCL12 (also known as stromal cell-derived factor-1, or SDF-1) regulate a broad range of physiological functions. Dysregulation of the CXCL12/CXCR4 axis is involved in numerous pathological conditions such as HIV infection, inflammation and cancer. Herein, we report the design, synthesis, and characterization of novel CXCR4 antagonists based on cyclic amine scaffolds. Compound 24 was identified as a potent CXCR4 receptor antagonist (competitive inhibition of 12G5 binding, IC50=24 nM; functional inhibition of CXCL12-induced cytosolic calcium increase, IC50=0.1 nM). In addition, compound 24 potently inhibited cell migration in CXCR4/CXCL12-mediated chemotaxis in a matrigel invasion assay. The absolute configuration of compound 24 was elucidated by X-ray crystallography.

Design, synthesis, and evaluation of novel CXCR4 antagonists based on an aminoquinoline template

The chemokine receptor CXCR4 has been explored as a drug target due to its involvement in pathological conditions such as HIV infection and cancer metastasis. Here we report the structure–activity relationship study of novel CXCR4 antagonists based on an aminoquinoline template. This template is devoid of the chiral center in the classical tetrahydroquinoline (THQ) ring moiety and therefore can be easily synthesized. A number of potent CXCR4 antagonists were identified, exemplified by compound 3, which demonstrated excellent binding affinity with CXCR4 receptor (IC50 = 57 nM) and inhibited CXCL12 induced cytosolic calcium increase (IC50 = 0.24 nM). Furthermore, compound 3 potently inhibited CXLC12/CXCR4 mediated cell migration in a transwell invasion assay. The simplified synthetic approach combined with good physicochemical properties (e.g. MW 362, clogP 2.1, PSA 48, pKa 7.0 for compound 3) demonstrate the potential of this aminoquinoline template as a novel scaffold to develop CXCR4 antagonists.

HETEROARYL COMPOUNDS AS CXCR4 INHIBITORS, COMPOSITION AND METHOD USING THE SAME

The present disclosure provides heteroaryl compounds of Formula (I), processes for their preparation, pharmaceutical compositions containing them, and their use in the treatment of diseases and disorders, arising from or related to the CXCR4 pathway.

Sulfonyl-morpholino-pyrimidines: SAR and development of a novel class of selective mTOR kinase inhibitor

High throughput screening to identify inhibitors of the mTOR kinase revealed sulfonyl-morpholino-pyrimidine 1 as an attractive start point. The compound displayed good physicochemical properties and selectivity over related kinases such as PI3Kα. Library preparation of related analogs allowed the establishment of additional SAR understanding and in particular the requirement for a key hydrogen bond donor motif at the 4-position of the phenyl ring in compounds such as indole 19. Isosteric replacement of the indole functionality led to the identification of urea compounds such as 32 that show good levels of mTOR inhibition in both enzyme and cellular assays.

COMPOUNDS 947

A compound of formula (I) or a pharmaceutically acceptable salt thereof, processes for their preparation, pharmaceutical compositions containing them and their use in therapy, for example in the treatment of proliferative disease such as cancer and partic

COMPOUND - 946

A compound of formula (I) or a pharamaceutically acceptable salt thereof, processes for their preparation, pharmaceutical compositions containing them and their use intherapy, for example in the treatment of proliferative disease such as cancer and partic

MORPHOLINO PYRIMIDINE DERIVATIVES AND THEIR USE IN THERAPY

A compound of formula (I) or a salt, ester or prodrug thereof, processes for their preparation, pharmaceutical compositions containing them and their use in therapy, for example in the treatment of proliferative disease such as cancer and particularly in disease mediated by an mTOR kinase and/or one or more PI3K enzyme.

NOVEL INDOLE DERIVATES AS FABP-4 INHIBITORS

The present invention relates to novel compounds (I) wherein R0, R1, R2, R3, R4, R5, R6, R7, R8, A, B, n, X, and Y are as defined in the description and claims; and also to pharmaceutical compositions comprising the compounds, as well as to the use of the compounds in medicine and for the preparation of a medicament, which acts on the fatty acid binding protein FABP-4. The present invention relates to novel compounds (I) wherein R0, R1, R2, R3, R4, R5, R6, R7, R8, A, B, n, X, and Y are as defined in the description and claims; and also to pharmaceutical compositions comprising the compounds, as well as to the use of the compounds in medicine and for the preparation of a medicament, which acts on the fatty acid binding protein FABP-4.

Synthesis and biological evaluation of 2-methoxy- and 2-Methylthio-6-[(2'-alkylamino)ethyl]-4(3H)-pyrimidinones with anti-rubella virus activity

The synthesis of a new family of antiviral compounds, 2-methoxy-, and 2-methylthio-6-[(2'-alkylamino)ethyl]-4(3H)-pyrimidinones, has been accomplished. The activity of these agents against positive strand (rubella virus and sindbis virus) and negative str

Chloromethyl Substituted Heterocycles from Methyl Chlorotetrolate

Reaction of amidines, isothioureas or thioureas with methyl chlorotetrolate 1 leads to pyrimidin-4-ones 2 and 1,3-thiazines (3), respectively.Compounds 2 and 3 are starting materials for the synthesis of 6-chloromethyl-uracils (4), 1,3-thiazine-2,4-dione 5 and 6-benzylthiomethyl-thiazinone (6). 2-Aminothiazoles react with the ester 1 to yield 5-chloromethyl-thiazolopyrimidin-7-ones (7).The 5-oxo isomers 8 are obtained by reaction of thiazoles with ethyl γ-chloroacetoacetate.By reaction of 2-mercaptoimidazoles and 1 or chlorotetrolic acid the condensed 1,3-thiazinones (10) result.In the latter case the intermediate 9 is isolated.It can be cyclised to 10 by heating with acetic anhydride and sulphuric acid.