259809-79-5

Basic information

• Product Name: TERT-BUTYL 7,8-DIHYDRO-2-(METHYLSULFONYL)PYRIDO[4,3-D]PYRIMIDINE-6(5H)-CARBOXYLATE
• Synonyms: tert-butyl 7;tert-butyl 2-Methanesulfonyl-5H,6H,7H,8H-pyrido[4,3-d]pyriMidine-6-carboxylate;2-Methanesulfonyl-7,8-dihydro-5H-pyrido[4,3-d]pyriMidine -6-carboxylic acid tert-butyl ester;pyrido[4,3-d]pyrimidine-6(5H);tert-Butyl 7,8-dihydro-2-(methylsulfonyl);TERT-BUTYL 7,8-DIHYDRO-2-(METHYLSULFONYL)PYRIDO[4,3-D]PYRIMIDINE-6(5H)-CARBOXYLATE;8-dihydro-2-(Methylsulfonyl)pyrido[4
• CAS NO: 259809-79-5
• Molecular Formula: C₁₃H₁₉N₃O₄S
• Molecular Weight: 313.37
• Product Categories: pyrimidine;Heterocycle-Pyrimidine series;CHIRAL CHEMICALS
• Mol File: 259809-79-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 495.624 °C at 760 mmHg
• Flash Point: 253.544 °C
• Appearance: /
• Density: 1.291g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.543
• Storage Temp.: 2-8°C
• PKA: -1.86±0.20(Predicted)
• CAS DataBase Reference: TERT-BUTYL 7,8-DIHYDRO-2-(METHYLSULFONYL)PYRIDO[4,3-D]PYRIMIDINE-6(5H)-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL 7,8-DIHYDRO-2-(METHYLSULFONYL)PYRIDO[4,3-D]PYRIMIDINE-6(5H)-CARBOXYLATE(259809-79-5)
• EPA Substance Registry System: TERT-BUTYL 7,8-DIHYDRO-2-(METHYLSULFONYL)PYRIDO[4,3-D]PYRIMIDINE-6(5H)-CARBOXYLATE(259809-79-5)

Safety Data

• Hazardous Substances Data: 259809-79-5(Hazardous Substances Data)

Usage

General Description

TERT-BUTYL 7,8-DIHYDRO-2-(METHYLSULFONYL)PYRIDO[4,3-D]PYRIMIDINE-6(5H)-CARBOXYLATE is a chemical compound with a complex molecular structure. It is a pyrido-pyrimidine derivative that contains a tert-butyl ester group and a methylsulfonyl substituent. TERT-BUTYL 7,8-DIHYDRO-2-(METHYLSULFONYL)PYRIDO[4,3-D]PYRIMIDINE-6(5H)-CARBOXYLATE is mainly used as a potential drug candidate or as a precursor in the synthesis of pharmaceuticals. It may also have applications in various biochemical and medicinal research studies. Further research and analysis of this chemical's properties and potential uses are ongoing.

InChI:InChI=1/C13H19N3O4S/c1-13(2,3)20-12(17)16-6-5-10-9(8-16)7-14-11(15-10)21(4,18)19/h7H,5-6,8H2,1-4H3

Upstream product

• 157327-41-8 t-butyl-3-[(dimethylamino)methylidene]-4-oxopiperidine-1-carboxylate 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 259809-78-4 t-butyl-2-(methylthio)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-6-carboxylate 

Downstream Products

• 578713-43-6 N,N-Dimethyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine 
• 1365155-89-0 6-(4-(Benzyl(methyl)amino)cyclohexyl)-N,N-dimethyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2-amine 
• 1365155-94-7 tert-Butyl 4-(2-(dimethylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)cyclohexyl(methyl)carbamate 
• 1365154-07-9 N,N-dimethyl-6-(4-(methylamino)cyclohexyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2-amine 
• 1567964-27-5 6-(5'-chloro-3,5-dimethyl-2,4'-bipyridin-2'-yl)-N-phenyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine 
• 124458-31-7 5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine 
• 869198-95-8 2-amino-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-carboxylic acid tert-butyl ester 
• 1567963-78-3 6-(5-chloro-4-(quinolin-2-yl)pyridin-2-yl)-N-cyclopropyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine 
• 1567965-09-6 tert-butyl 2-(cyclopropylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate 

Relevant articles and documents

Design, Synthesis, and Structure-Activity Relationship of Tetrahydropyrido[4,3-d]pyrimidine Derivatives as Potent Smoothened Antagonists with in Vivo Activity

Medulloblastoma is one of the most prevalent brain tumors in children. Aberrant hedgehog (Hh) pathway signaling is thought to be involved in the initiation and development of medulloblastoma. Vismodegib, the first FDA-approved cancer therapy based on inhibition of aberrant hedgehog signaling, targets smoothened (Smo), a G-protein coupled receptor (GPCR) central to the Hh pathway. Although vismodegib exhibits promising therapeutic efficacy in tumor treatment, concerns have been raised from its nonlinear pharmacokinetic (PK) profiles at high doses partly due to low aqueous solubility. Many patients experience adverse events such as muscle spasms and weight loss. In addition, drug resistance often arises among tumor cells during treatment with vismodegib. There is clearly an urgent need to explore novel Smo antagonists with improved potency and efficacy. Through a scaffold hopping strategy, we have identified a series of novel tetrahydropyrido[4,3-d]pyrimidine derivatives, which exhibited effective inhibition of Hh signaling. Among them, compound 24 is three times more potent than vismodegib in the NIH3T3-GRE-Luc reporter gene assay. Compound 24 has a lower melting point and much greater solubility compared with vismodegib, resulting in linear PK profiles when dosed orally at 10, 30, and 100 mg/kg in rats. Furthermore, compound 24 showed excellent PK profiles with a 72% oral bioavailability in beagle dogs. Compound 24 demonstrated overall favorable in vitro safety profiles with respect to CYP isoform and hERG inhibition. Finally, compound 24 led to significant regression of subcutaneous tumor generated by primary Ptch1-deficient medulloblastoma cells in SCID mouse. In conclusion, tetrahydropyrido[4,3-d]pyrimidine derivatives represent a novel set of Smo inhibitors that could potentially be utilized to treat medulloblastoma and other Hh pathway related malignancies.

Substituted Benzamide Compounds

Substituted benzamide compounds corresponding to formula (I) in which R5, R6, R7, R8, a, b, c, d, t, D and X have defined meanings, a process for their preparation, pharmaceutical compositions comprising such compounds, and a method of using such compounds to treat pain and other conditions mediated at least in part via the bradykinin 1 receptor.