171178-33-9

Basic information

• Product Name: 6-chloropyrido[3,2-d]pyrimidin-4(3H)-one
• Synonyms: 6-chloropyrido[3,2-d]pyrimidin-4(3H)-one;6-chloro-3H,4H-pyrido[3,2-d]pyriMidin-4-one;6-Chloropyrido[3,2-d]pyrimidin-4(1H)-one
• CAS NO: 171178-33-9
• Molecular Formula: C₇H₄ClN₃O
• Molecular Weight: 182
• EINECS: 604-604-1
• Mol File: 171178-33-9.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 400.766 °C at 760 mmHg
• Flash Point: 196.176 °C
• Appearance: /
• Density: 1.66
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.749
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -1.03±0.20(Predicted)
• CAS DataBase Reference: 6-chloropyrido[3,2-d]pyrimidin-4(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-chloropyrido[3,2-d]pyrimidin-4(3H)-one(171178-33-9)
• EPA Substance Registry System: 6-chloropyrido[3,2-d]pyrimidin-4(3H)-one(171178-33-9)

Safety Data

• Hazardous Substances Data: 171178-33-9(Hazardous Substances Data)

Usage

General Description

6-chloropyrido[3,2-d]pyrimidin-4(3H)-one is a chemical compound with the molecular formula C8H5ClN2O. It belongs to the pyrido[3,2-d]pyrimidinone family and is a heterocyclic compound, containing both nitrogen and oxygen in its ring structure. This chemical is a chlorinated derivative of pyrido[3,2-d]pyrimidin-4(3H)-one, and it is often used as a building block in organic synthesis and pharmaceutical research. It has potential applications in the development of novel drugs and bioactive molecules due to its unique structural features and reactivity. Furthermore, this compound also serves as a valuable intermediate in the production of various agrochemicals, pharmaceuticals, and other fine chemicals.

InChI:InChI=1/C7H4ClN3O/c8-5-2-1-4-6(11-5)7(12)10-3-9-4/h1-3H,(H,9,10,12)

Upstream product

• 122-51-0 orthoformic acid triethyl ester 
• 175358-01-7 3-amino-6-chloro-pyridine-2-carboxylic acid amide 
• 93683-65-9 6-chloro-3-nitropicolinonitrile 
• 171178-21-5 6-chloro-3-nitropyridine-2-carboxamide 
• 16013-85-7 2,6-dicholoro-3-nitropyridine 
• 2402-78-0 2,6-dichloropyridine 
• 14036-06-7 diethoxymethyl acetate 

Downstream Products

• 175358-02-8 4,6-dichloropyrido<3,2-d>pyrimidine 
• 897361-24-9 6-(4-fluorophenyl)-pyrido[3,2-d]pyrimidin-4(3H)one 
• 897359-55-6 6-(3,4-dimethoxyphenyl)pyrido[3,2-d]pyrimidin-4(3H)-one 
• 897360-67-7 6-(3-methyl-4-methoxyphenyl)pyrido[3,2-d]pyrimidin-4(3H)one 
• 1135310-04-1 N-(5-(4-dimethylaminopyrido[3,2-d]pyrimidin-6-yl)-3-pyridinyl)benzenesulfonamide 
• 1135310-05-2 N-(5-(4-(4-morpholinyl)pyrido[3,2-d]pyrimidin-6-yl)-3-pyridinyl)benzenesulfonamide 
• 1400632-57-6 N-(1H-benzimidazol-2-ylmethyl)-6-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrido[3,2-d]pyrimidin-4-amine 
• 1400633-17-1 4-chloro-6-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrido[3,2-d]pyrimidine 
• 1400633-05-7 6-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrido[3,2-d]pyrimidin-4-amine 
• 1400632-89-4 N-{6-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrido[3,2-d]pyrimidin-4-yl}-1-(morpholin-4-ylmethyl)cyclopropanecarboxamide 
• 1400633-16-0 4-chloro-6-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrido[3,2-d]pyrimidine 
• 1400667-72-2 N-(5-(4-(tetrahydro-2H-pyran-4-yloxy)pyrido[3,2-d]pyrimidin-6-yl)pyridin-3-yl)benzenesulfonamide 
• 1400667-73-3 N-(2-chloro-5-(4-(tetrahydro-2H-pyran-4-yloxy)pyrido[3,2-d]pyrimidin-6-yl)pyridin-3-yl)-2,4-difluorobenzenesulfonamide 
• 1400667-74-4 N-(5-(4-(tetrahydro-2H-pyran-4-yloxy)pyrido[3,2-d]pyrimidin-6-yl)pyridin-3-yl)-2,4-difluorobenzenesulfonamide 

Relevant articles and documents

Optimization of 4,6-Disubstituted Pyrido[3,2-d]pyrimidines as Dual MNK/PIM Inhibitors to Inhibit Leukemia Cell Growth

Mitogen-activated protein kinase-interacting kinases (MNKs) and provirus integration in maloney murine leukemia virus kinases (PIMs) are downstream enzymes of cell proliferation signaling pathways associated with the resistance of tyrosine kinase inhibitors. MNKs and PIMs have complementary effects to regulate cap-dependent translation of oncoproteins. Dual inhibitors of MNKs and PIMs have not been developed. We developed a novel 4,6-disubstituted pyrido[3,2-d]pyrimidine compound 21o with selective inhibition of MNKs and PIMs. The IC50’s of 21o to inhibit MNK1 and MNK2 are 1 and 7 nM and those to inhibit PIM1, PIM2, and PIM3 are 43, 232, and 774 nM, respectively. 21o inhibits the growth of myeloid leukemia K562 and MOLM-13 cells with GI50’s of 2.1 and 1.2 μM, respectively. 21o decreases the levels ofp-eIF4E andp-4EBP1, the downstream products of MNKs and PIMs, as well as cap-dependent proteins c-myc, cyclin D1, and Mcl-1. 21o inhibits the growth of MOLM-13 cell xenografts without causing evident toxicity. 21o represents an innovative dual MNK/PIM inhibitor with a good pharmacokinetic profile.

4, 6-disubstituted pyridine [3, 2-d] pyrimidine compound as well as preparation and application thereof

The invention belongs to the technical field of medicines. The invention relates to the field of pharmaceutical chemistry, in particular to a 4, 6-disubstituted pyridine [3, 2-d] pyrimidine compound and pharmaceutically acceptable salt thereof, a preparation method of the compound, a pharmaceutical composition taking the compound as an active ingredient, and application of the compound in preparation of an MNK inhibitor and drugs for treating and/or preventing various cancers and/or metabolic diseases. The present invention relates to compounds represented by formulas I, II, III or IV, and pharmaceutically acceptable salts, hydrates, solvates and metabolites thereof, wherein the variables are described in the claims and the description.

Discovery of selective 4-amino-pyridopyrimidine inhibitors of MAP4K4 using fragment-based lead identification and optimization

Mitogen-activated protein kinase kinase kinase kinase 4 (MAP4K4) is a serine/threonine kinase implicated in the regulation of many biological processes. A fragment-based lead discovery approach was used to generate potent and selective MAP4K4 inhibitors. The fragment hit pursued in this article had excellent ligand efficiency (LE), an important attribute for subsequent successful optimization into drug-like lead compounds. The optimization efforts eventually led us to focus on the pyridopyrimidine series, from which 6-(2-fluoropyridin-4-yl)pyrido[3,2-d]pyrimidin-4-amine (29) was identified. This compound had low nanomolar potency, excellent kinase selectivity, and good in vivo exposure, and demonstrated in vivo pharmacodynamic effects in a human tumor xenograft model.