339016-18-1

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
4-CHLORO-6-MORPHOLIN-4-YLPYRIMIDIN-2-AMINE is utilized as a key component in the development of new medications due to its potential therapeutic effects on a range of diseases. Its unique structural features allow it to be a versatile building block in the synthesis of novel pharmaceutical compounds, enhancing the discovery of effective treatments.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 4-CHLORO-6-MORPHOLIN-4-YLPYRIMIDIN-2-AMINE is employed as a subject of study for its promising biological activities. Researchers are interested in its properties to understand better how it can be harnessed for the development of new drugs and therapies, making it an important target for investigation and advancement in medicinal applications.

InChI:InChI=1/C8H11ClN4O/c9-6-5-7(12-8(10)11-6)13-1-3-14-4-2-13/h5H,1-4H2,(H2,10,11,12)

Upstream product

• 110-91-8 morpholine 
• 56-05-3 2-Amino-4,6-dichloropyrimidine 

Downstream Products

• 1072269-82-9 (4-chloro-6-morpholin-4-yl-pyrimidin-2-ylmethyl)-phenethyl-amine 
• 1072270-14-4 (4-chloro-6-morpholin-4-yl-pyrimidin-2-ylmethyl)-triphenyl-phosphonium bromide 
• 343373-72-8 4-(6-chloro-2-phenyl-pyrimidin-4-yl)-morpholine 

Relevant academic research and scientific papers

PIKFYVE KINASE INHIBITORS

The present invention relates to compounds useful as inhibitors of phosphatidylinositol-3-phosphate 5-kinase (PIKfyve) as well as their use for treating diseases and disorders associated with PIKfyve.

Exploration of carbamide derived pyrimidine-thioindole conjugates as potential VEGFR-2 inhibitors with anti-angiogenesis effect

The development of new small molecules from known structural motifs through molecular hybridization is one of the trends in drug discovery. In this connection, we have combined the two pharmacophoric units (pyrimidine and thioindole) in a single entity via molecular hybridization strategy along with introduction of urea functionality at C2 position of pyrimidine to increase the efficiency of H-bonding interactions. Among the synthesized conjugates 12a-aa, compound 12k was found to exhibit significant IC50 values 5.85, 7.87, 6.41 and 10.43 μM against MDA-MB-231 (breast), HepG2 (liver), A549 (lung) and PC-3 (prostate) cancer cell lines, respectively. All these compounds were further evaluated for their inhibitory activities against VEGFR-2 protein. The results specified that among the tested compounds, 12d, 12e, 12k, 12l, 12p, 12q, 12t and 12u prominently suppressed VEGFR-2, with IC50 values of 310–920 nM in association to the positive control (210 nM). Angiogenesis inhibition was evident by tube formation assay in HUVECs and cell-invasion by transwell assay. The mechanism of cellular toxicity on MDA-MB-231 was found through depolarisation of mitochondrial membrane potential, increased ROS production and subsequent DNA damage resulting in apoptosis induction. Moreover, clonogenic and wound healing assays designated the inhibition of colony formation and cell migration by 12k in a dose-dependent manner. Molecular docking studies also shown that compound 12k capably intermingled with catalytically active residues GLU-885, ASP-1046 of the VEGFR-2 through hydrogen-bonding interactions.

Investigation of novel pesticides with insecticidal and antifungal activities: Design, synthesis and SAR studies of benzoylpyrimidinylurea derivatives

In order to find pesticides with insecticidal and antifungal activities, a series of novel benzoyl pyrimidinylurea derivatives were designed and synthesized. All target compounds were identified by 1H-NMR spectroscopy and HRMS. Insecticidal and antifungal activity of these compounds were evaluated and the structure-activity relationships (SAR) were clearly and comprehensively illustrated. Compound 7, with low toxicity to zebrafish (LC50 = 378.387 μg mL?1) showed 100% inhibition against mosquito (Culex pipiens pallens) at 0.25 μg mL?1. Both compounds 19 and 25 exhibited broad-spectrum fungicidal activity (>50% inhibitory activities against 13 phytopathogenic fungi), which were better than those of the commercial pesticide pyrimethanil (>50% inhibitory activities against eight phytopathogenic fungi). Furthermore, compounds 19 and 25 exhibited protective activity against Sclerotinia sclerotiorum on leaves of Brassica oleracea L. during in vivo experiments.

A novel benzoyl pyrimidine urea compound and its preparation and use (by machine translation)

The invention provides a benzoyl pyrimidine urea compound, of formula I or formula II structure shown. The present invention provides benzoyl pyrimidine urea compound has excellent armyworm killing, mosquito killing and broad-spectrum antifungal activity. The experimental result shows, the present invention provides benzoyl pyrimidine urea compound in 0.5 μg mL- 1 Sliding surface of larvae activity can be up to 100%, in the 0.25μg mL- 1 Sliding surface of larvae activity can be up to 100%. In the 50 μg mL- 1 When, demonstrated broad-spectrum antifungal activity, and to the cabbage in vitro blade has a certain protective effect. And low toxicity to fish, LC to the zebra fish50 Are respectively 378.387 mg L- 1 , 21.668 Mg L- 1 . Can be used to prepare insecticidal, anti-plant-pathogenic fungi pesticide application. (by machine translation)

ACETYLCHOLINE BINDING PROTEIN LIGANDS, COOPERATIVE NACHR MODULATORS AND METHODS FOR MAKING AND USING

The invention provides compositions and methods a) for increasing or stimulating the release of other transmitters (excitatory amino acids, inhibitor amino acids and biogenic amines) in the central nervous system (CNS) or the brain, or modulating, decreas

PHARMACEUTICAL COMPOUNDS

The invention provides compounds which are pyrimidines of formula (I): wherein R2 is bonded at ring position 2 and -YR1 is bonded at ring position 5 or 6, or YR1 is bonded at ring position 2 and R2 is bonded at ring position 6; R is an indol-4-yl group which is substituted at the 5- or 6-position; either: (a) Y is selected from -O-(CH2)n-, -NH-(CH2)n-,. -NHC(O)-(CH2)n and -C(O)NH-(CH2)n- wherein n is 0 or an integer of 1 to 3, and R1 is selected from an unsaturated 5- to 12-membered carbocyclic or heterocyclic group which is unsubstituted or substituted and a group -NR3R4 wherein R3 and R4, which are the same or different, are each independently selected from H, C1-C6 alkyl which is unsubstituted or substituted, C3 - C10 cycloalkyl which is unsubstituted or substituted, -C(O)R, -C(O)N(R)2 and -S(O)mR, or R3 and R4 together form, with the nitrogen atom to which they are attached, a saturated 5-, 6- or 7- membered N-containing heterocyclic group which is unsubstituted or substituted; (b) Y is a direct bond and R1 is selected from an unsaturated 5- to 12-membered carbocyclic or heterocyclic group which is unsubstituted or substituted, and a group -NR3R4 wherein R3 and R4, which are the same or different, are each independently selected from H, C1-C6 alkyl which is unsubstituted or substituted, C3-C10 cycloalkyl which is unsubstituted or substituted, -C(O)R, -C(O)N(R)2 and -S(O)mR; R is selected from H, C1-C6 alkyl, C3-C10 cycloalkyl and a 5- to 12-membered aryl or heteroaryl group, which group is unsubstituted or substituted; and m is 1 or 2; or a pharmaceutically acceptable salt thereof. These compounds are inhibitors of PO K and may thus be used to treat diseases and disorders arising from abnormal cell growth, function or behaviour associated with PB kinase such as cancer, immune disorders, cardiovascular disease, viral infection, inflammation, metabolism/endocrine function disorders and neurological disorders.

PHARMACEUTICAL COMPOUNDS

The invention provides a compound which is a pyrimidine of formula (I): The compounds are inhibitors of PI3K and may thus be used to treat diseases and disorders arising from abnormal cell growth, function or behaviour associated with PI3 kinase such as cancer, immune disorders, cardiovascular disease, viral infection, inflammation, metabolism/endocrine function disorders and neurological disorders.

Two polymorphs, with z′ = 1 and 2, of 2-amino-4-chloro-6-morpholinopyrimidine in P21/c, and 2-amino-4-chloro-6-piperidinopyrimidine, which is isomorphous and almost isostructural with the Z′ = 2 polymorph

Crystallization of 2-amino-4-chloro-6-morpholinopyrimidine, C8H11ClN4O, (I), yields two polymorphs, both with space group P21/c, having Z′ = 1 (from diethyl ether solution) and Z′ = 2 (from dichloromethane solution), denoted (Ia) and (Ib), respectively. In polymorph (Ia), the molecules are linked by an N-H...O and an N-H...N hydrogen bond into sheets built from alternating R22(8) and R66(40) rings. In polymorph (Ib), one molecule acts as a triple acceptor of hydrogen bonds and the other acts as a single acceptor; one N-H...O and three N-H...N hydrogen bonds link the molecules in a complex chain containing two types of R22(8) and one type of R22(18) ring. 2-Amino-4-chloro-6-piperidinopyrimidine, C9H13ClN4, (II), which is isomorphous with polymorph (Ib), also has Z′ = 2 in P21/c, and the molecules are linked by three N-H...N hydrogen bonds into a centrosymmetric four-molecule aggregate containing three R22(8) rings.