116705-41-0

Basic information

• Product Name: (E)-6-(2-(dimethylamino)vinyl)-5-nitropyrimidine-2,4(1H,3H)-dione
• Synonyms: (E)-6-(2-(dimethylamino)vinyl)-5-nitropyrimidine-2,4(1H,3H)-dione
• CAS NO: 116705-41-0
• Molecular Weight: 226.192
• Mol File: 116705-41-0.mol

Chemical Properties

• CAS DataBase Reference: (E)-6-(2-(dimethylamino)vinyl)-5-nitropyrimidine-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-6-(2-(dimethylamino)vinyl)-5-nitropyrimidine-2,4(1H,3H)-dione(116705-41-0)
• EPA Substance Registry System: (E)-6-(2-(dimethylamino)vinyl)-5-nitropyrimidine-2,4(1H,3H)-dione(116705-41-0)

Safety Data

• Hazardous Substances Data: 116705-41-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(E)-6-(2-(dimethylamino)vinyl)-5-nitropyrimidine-2,4(1H,3H)-dione is used as an intermediate or starting material for the synthesis of various pharmaceuticals and organic compounds. Its unique structure and functional groups make it a valuable building block in the production of biologically active molecules and materials.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (E)-6-(2-(dimethylamino)vinyl)-5-nitropyrimidine-2,4(1H,3H)-dione is used as a key component in the development of new drugs and therapeutic agents. Its versatile structure allows for the creation of molecules with specific biological activities, targeting various diseases and medical conditions.
Used in Synthetic Chemistry:
(E)-6-(2-(dimethylamino)vinyl)-5-nitropyrimidine-2,4(1H,3H)-dione is also utilized in synthetic chemistry as a precursor for the synthesis of a wide range of organic compounds. (E)-6-(2-(dimethylamino)vinyl)-5-nitropyrimidine-2,4(1H,3H)-dione's functional groups provide opportunities for further chemical modifications, making it a versatile building block for the creation of novel materials and compounds with specific properties and applications.

Upstream product

• 16632-21-6 5-nitro-6-methyluracil 
• 1188-33-6 N,N-dimethylformamide diethyl diacetal 
• 626-48-2 6-Methyluracil 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 

Downstream Products

• 114684-99-0 2-Chloro-4-(β-hydroxyethylamino)pyrrolo<3,2-d>pyrimidine 
• 114684-95-6 2-Chloro-4-piperidin-1-yl-5H-pyrrolo[3,2-d]pyrimidine 
• 114685-00-6 (2-Chloro-5H-pyrrolo[3,2-d]pyrimidin-4-yl)-(2-cyclohexyl-ethyl)-amine 
• 114684-97-8 4-(2-Chloro-5H-pyrrolo[3,2-d]pyrimidin-4-ylamino)-butyric acid 
• 114684-98-9 (2-Chloro-5H-pyrrolo[3,2-d]pyrimidin-4-yl)-(1-methyl-2-phenyl-ethyl)-amine 
• 114684-94-5 2-Chloro-4<β-(cyclohexen-1'-yl)ethylamino>pyrrolo<3,2-d>pyrimidine 
• 114684-96-7 2-Chloro-4-morpholin-4-yl-5H-pyrrolo[3,2-d]pyrimidine 
• 114685-04-0 N²,N⁴-Diphenyl-5H-pyrrolo[3,2-d]pyrimidine-2,4-diamine 
• 114685-02-8 N²,N⁴-Bis-(4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-2,4-diamine 
• 114685-01-7 2,4-Bis<(β-cyclohexen-1'-yl)ethylamino>pyrrolo<3,2-d>pyrimidine 
• 1377432-93-3 tert-butyl ((3R)-1-(3-(2-cyanobenzyl)-4-oxo-7-(thiophen-3-yl)-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-2-yl)piperidin-3-yl)carbamate 
• 1377432-74-0 2-((2-((R)-3-aminopiperidin-1-yl)-7-bromo-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-3-yl)methyl)benzonitrile 
• 1377432-75-1 2-((2-((R)-3-aminopiperidin-1-yl)-4-oxo-7-(pyridin-3-yl)-4H-pyrrolo[3,2-d]pyrimidin-3(5H)-yl)methyl)benzonitrile 
• 1377432-76-2 2-((2-((R)-3-aminopiperidin-1-yl)-4-oxo-7-(pyridin-4-yl)-4H-pyrrolo[3,2-d]pyrimidin-3(5H)-yl)methyl)benzonitrile 

Relevant articles and documents

Discovery of potent dipeptidyl peptidase IV inhibitors through pharmacophore hybridization and hit-to-lead optimization

A novel dipeptidyl peptidase IV inhibitor hit (5, IC50 = 0.86 μM) was structurally derived from our recently disclosed preclinical candidate 4 by replacing the cyanobenzyl with a butynyl based on pharmacophore hybridization. A hit-to-lead optimization effort was then initiated to improve its potency. Most N-substituted analogs exhibited good in vitro activity, and compound 18o (IC50 = 1.55 nM) was identified to be a potent dipeptidyl peptidase IV inhibitor with a significantly improved pharmacokinetic properties (bioavailablity: 41% vs 82.9%; T1/2: 2 h vs 4.9 h).

Structural and Biological Investigations for a Series of N-5 Substituted Pyrrolo[3,2-d]pyrimidines as Potential Anti-Cancer Therapeutics

Pyrrolo[3,2-d]pyrimidines have been studied for many years as potential lead compounds for the development of antiproliferative agents. Much of the focus has been on modifications to the pyrimidine ring, with enzymatic recognition often modulated by C2 and C4 substituents. In contrast, this work focuses on the N5 of the pyrrole ring by means of a series of novel N5-substituted pyrrolo[3,2-d]pyrimidines. The compounds were screened against the NCI-60 Human Tumor Cell Line panel, and the results were analyzed using the COMPARE algorithm to elucidate potential mechanisms of action. COMPARE analysis returned strong correlation to known DNA alkylators and groove binders, corroborating the hypothesis that these pyrrolo[3,2-d]pyrimidines act as DNA or RNA alkylators. In addition, N5 substitution reduced the EC50 against CCRF-CEM leukemia cells by up to 7-fold, indicating that this position is of interest in the development of antiproliferative lead compounds based on the pyrrolo[3,2-d]pyrimidine scaffold.

Pyrrolopyrimidine ketone compound and preparation method and application thereof

The invention relates to a pyrrolopyrimidine ketone compound and a preparation method and application thereof, and belongs to the technical field of medicine. The pyrrolopyrimidine ketone compound having a structural feature of formula I, or a pharmaceutically acceptable salt thereof has a very good inhibition effect on DPP-IV, and almost no effect on activity of DPP-VIII and DPP-IX, can effectively control the blood glucose concentration of diabetic rats, and is safe and low in toxicity through the verification of pharmacological and toxicological tests. After being prepared into a medicine, the compound provided by the invention not only has an obvious efficacy but also has very small side effects, thus greatly improving the administration convenience and patient use compliance, therefore, the compound has obvious advantages compared with the same kind of medicine. The formula is shown in the specification.

Novel pyrrolopyrimidine analogues as potent dipeptidyl peptidase IV inhibitors based on pharmacokinetic property-driven optimization

We previously reported a highly potent DPP-IV inhibitor 6 with low in vivo efficacy. While trying to maintain consistent in vitro and in vivo biological activity, we initiated a pharmacokinetic property-driven optimization to improve the metabolic stability and permeability of inhibitor 6. A simple scaffold replacement of thienopyrimidine with pyrrolopyrimidine (21a) led to significantly improved metabolic stability (4% vs. 65% remaining). Further modification of the pyrrolopyrimidine scaffold to produce compound 21j resulted in much better oral bioavailability than 6. Importantly, compound 21j exhibits greater in vivo efficacy than does 6 and Alogliptin and is worthy of further development.