168413-01-2

Usage

Molecular Weight

177.14 g/mol

Structure

A pyrimidine derivative with a propargyl group (-C≡CH3) attached to the 1-position.

Reactivity

Highly reactive due to the presence of the propargyl group.

Applications

Potential use in pharmaceuticals and materials science.

Antiviral and Antitumor Properties

PPD has been studied for its antiviral and antitumor properties.

Building Block

PPD can be used as a building block for the synthesis of new drugs.

Electronic and Optical Properties

Its unique chemical structure makes it an attractive candidate for the development of novel materials with specific electronic and optical properties.

Handling

PPD's reactivity and potential toxicity require careful handling.

Further Research

More research is needed to fully understand its properties and potential uses.

Upstream product

• 106-96-7 propargyl bromide 
• 66-22-8 uracil 
• 107-19-7 propargyl alcohol 
• 10457-14-4 O,O'-bis-(trimethylsilyl)uracil 

Downstream Products

• 168413-03-4 3-(4-methoxybenzyl)-1-propargyluracil 
• 1616268-43-9 (1S,2R,3R)-dibenzyl 4-{[4-(2,4-dioxopyrimidin-1-yl)methyl]-1H-1,2,3-triazol-1-yl}-1,2,3-trihydroxy-2,3-O-isopropylidenebutylphosphonate 
• 1616268-37-1 (1S,2R,3S)-dibenzyl 4-{[4-(2,4-dioxopyrimidin-1-yl)methyl]-1H-1,2,3-triazol-1-yl}-1,2,3-trihydroxy-2,3-O-isopropylidenebutylphosphonate 
• 1616268-25-7 (1R,2S)-dibenzyl 2-benzyloxy-3-{4-[(2,4-dioxopyrimidin-1-yl)methyl]-1H-1,2,3-triazol-1-yl}-1-hydroxypropylphosphonate 
• 1616268-11-1 (1S,2S)-dibenzyl 2-benzyloxy-3-{4-[(3,4-dihydro-2,4-dioxopyrimidin-1-yl)methyl]-1H-1,2,3-triazol-1-yl}-1-hydroxypropylphosphonate 
• 1391731-34-2 1-[((2,3,5-tri-O-benzoyl-β-D-erythro-pentofuranosyl)-1,2,3-triazol-4-yl)methyl]uracil 
• 1391731-30-8 1-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)pyrimidine-2,4-(1H,3H)-dione 
• 1355151-80-2 1-(3-(3,5-dimethoxyphenyl)prop-2-ynyl)uracil 
• 1355151-78-8 1-(3-(2-nitrophenyl)prop-2-ynyl)uracil 

Relevant academic research and scientific papers

Syntheses of 1,2,3-triazole-bridged pyranose sugars with purine and pyrimidine nucleobases and evaluation of their anticancer potential

With the aim to create a library of compounds with potential bioactivities by combining special characteristics of two important groups such as nucleobases and carbohydrates, twenty 1,4-disubstituted-triazole nucleosides were synthesized in good yields (80-94%) using the copper catalyzed ‘Click’ reaction between azido-modified pento- or hexopyranoses and alkyne-bearing pyrimidine or purine nucleobases. Structural elucidation was made with the assistance of spectroscopic techniques such as FTIR, 1D-, 2D-NMR, and ESI-TOFMS. All the synthesized triazole nucleosides were evaluated for their cytotoxic activity against three human cancer cell lines (MDA-MB-231, Hep3B, PC-3) by using the MTT assay. Particularly, compounds 3a and 1b were identified as potential hits against Hep3B cell.

Synthesis and biological evaluations of mono- and bis-ferrocene uracil derivatives

Mono- (3a–3e and 4a–4e) and bis-ferrocene (5a–5e and 6a–6e) conjugated 5-substituted uracil derivatives that are bridged by 1,2,3-triazole linker were synthesized. The impact of ferrocene unit and spacer between ferrocene and triazole on radical scavenging potency was observed. Bis-ferrocenyl uracil derivatives exhibited better antiproliferative activities than their mono-ferrocenyl analogs. Bis-ferrocenyl methyl- (5b) and halogen-substituted (5e, 6c, and 6d) uracil derivatives showed pronounced and selective cytostatic activities on colon adenocarcinoma (CaCo-2) and Burkitt lymphoma (Raji) cells, with higher potency and selectivity than the reference drug 5-fluorouracil. Generation of reactive oxygen species (ROS) in CaCo-2 and Raji cells when treated with compounds 5b, 5e, and 6d was observed. Bis-ferrocenyl 5-chlorouracil 6c induced significant disruption in mitochondrial membrane potential that is accompanied by activation of apoptosis in CaCo-2, Raji, and acute lymphoblastic leukemia (CCRF-CEM) cells, while 6d caused mitochondrial dysfunction and apoptosis induction in CaCo-2 and Raji cells. Potent antiproliferative activity of 6c and 6d could be associated with mitochondrial membrane potential disruption accompanied by apoptosis induction. Our findings highlighted 6c and 6d with potent and selective antiproliferative activity on CaCo-2, Raji, and CCRF-CEM cells that may be associated with targeting cancer cell mitochondria, as a molecular target.

A new dual-responsive organogel based on uracil-appended glycyrrhetinic acid

A novel functional tweezer based on uracil-appended glycyrrhetinic acid with excellent gelation ability was synthesized, and the gel could transform to sol by F- and Hg2+.

Benzenesulfonamides incorporating nitrogenous bases show effective inhibition of β-carbonic anhydrases from the pathogenic fungi Cryptococcus neoformans, Candida glabrata and Malassezia globosa

There is an urgent need for new chemotherapic agents to treat human fungal infections due to emerging and spreading globally resistance mechanisms. Among the new targets that have been recently investigated for the development of antifungal drugs there are the metallo-enzymes Carbonic Anhydrases (CAs, EC 4.2.1.1). The inhibition of the β-CAs identified in many pathogenic fungi leads to an impairment of parasite growth and virulence, which in turn leads to a significant anti-infective effect. Based on antifungal nucleoside antibiotics, the inhibition of the β-CAs from the resistance-showing fungi Candida glabrata (CgNce103), Cryptococcus neoformans (Can2) and Malasszia globosa (MgCA) with a series of benzenesulfonamides bearing nitrogenous bases, such as uracil and adenine, is here reported. Many such compounds display low nanomolar (100 nM) inhibitory potency against Can2 and CgNce103, whereas the activity of MgCA is considerably less affected (inhibition constants in the range 138.8–5601.5 nM). The β-CAs inhibitory data were compared with those against α-class human ubiquitous isoforms. Interesting selective inhibitory activities for the target fungal CAs over hCA I and II were reported, which make nitrogenous base benzenesulfonamides interesting tools and leads for further investigations in search of new antifungal with innovative mechanisms of action.

A novel approach towards studying non-genotoxic enediynes as potential anticancer therapeutics.

A novel uracil-containing enediyne was synthesized by the fusion at N(1) and N(3) of uracil with an 11-membered cyclic enediyne. Compound was found to be stable against cycloaromatization at 80 degreesC. Thus, it did not cause DNA-damage. Unlike other alkylated uracil derivatives 2--6, highly strained uracil-containing enediyne was reacted with methyl thioglycolate at 25 degreesC to produce uracil () and linear enediyne. This reactivity toward a sulfhydryl group may play a significant role in the mechanism by which compound directed its cytotoxicity toward tumor cell lines. Tumor cells were found to be more susceptible to enediyne than normal human embryonic lung cells. A combination of with adriamycin or 1-(beta-D-arabinofuranosyl)cytosine resulted in synergistic anticancer activity against murine L1210 and P388 leukemias, Sarcoma 180, and human CCRF--CEM lymphoblastic leukemia. After treatment of Molt-4 cells with uracil-containing enediyne, light microscope examination demonstrated the presence of cell shrinkage and nuclear segmentation. Treatment of cultured Molt-4 human leukemia cells with enediyne resulted in a time-dependent depletion of glutathione (GSH) whereas the exposure of the cells to the GSH precursor N-acetylcysteine (NAC) resulted in a substantial suppression of this effect. As such, involvement of GSH depletion in the process of apoptosis may explain the mechanism of action of non-genotoxic enediyne against malignant tumor cell lines.

Synthesis and transfer of chirality in supramolecular hydrogen bonded conjugated diblock copolymers

The synthesis of a block copoly(3-alkylthiophene) consisting of two different P3AT blocks equipped with an H-donor and -acceptor functionality is presented. The P3ATs were synthesized using a functionalized Ni-initiator. By a series of postpolymerization reactions, including click chemistry, an H-donor and -acceptor entity was attached to the end of the polymer chains. Evidence for a quantitative functionalization of the polymers was provided by 1H NMR and MALDI-ToF analyses. Chiral side chains were implemented on one of both blocks, allowing the study of the influence of the H-bond formation on the chiral self-assembly using UV-vis and circular dichroism spectroscopy.

Synthesis of new 1,2,3-triazole acyclonucleoside analogues of ACV and HBG

1,3-dipolar cycloaddition of N-9/N-1-propargylpurine/pyrimidine to the corresponding azidocompounds 9-10 produces acyclonucleoside analogues 13a-h, 14a-h in which the 4-methyl-1,2,3-triazole is used as spacer arm.

Triphenylphosphonium conjugates of 1,2,3-triazolyl nucleoside analogues. Synthesis and cytotoxicity evaluation

A series of triphenylphosphonium (TPP) conjugates of 1,2,3-triazolyl analogues of several pyrimidine nucleosides was synthesized and evaluated for the in vitro cytotoxicity against human cancer cell lines M-HeLa, MCF-7, PANC-1, PC-3, DU145, SKOV-3, A275,

Synthesis of novel pyrimidine nucleoside analogues owning multiple bases/sugars and their glycosidase inhibitory activity

A series of novel nucleoside analogues having dual bases (pyrimidine and triazole) and sugars have been synthesized by CuAAC reaction of azido sugars with propynylated pyrimidines. These compounds were evaluated for their in vitro α-glucosidase inhibitory

Synthesis of 3'-deoxy-3' and 5'-deoxy-5'-[4-(purin-9-yl/pyrimidin-1- yl)methyl-1,2,3-triazol-1-yl]thymidine via 1,3-dipolar cycloaddition

Synthesis of new 3'-deoxy-3' and 5'-deoxy-5'-[(4-(purin-9-yl/pyrimidin- 1-yl)methyl-1,2,3-Triazol-1-yl]thymidine 8a-g, 10a-g from 3'-azido-3'-deoxy- 5'-O-monomethoxytrityl-thymidine and 5'-azido-5'-deoxythymidine respectively are described. The key step is the 1,3-dipolar cycloaddition between the azido group and N-9/N-1-propargylpurine/pyrimidine derivatives.