28485-18-9

Usage

Uses

Used in Pharmaceutical Industry:
2,4-DIOXO-1,2,3,4-TETRAHYDROPYRIMIDINE-5-SULFONYL CHLORIDE is used as a pharmaceutical intermediate for the synthesis of various therapeutic agents. Its unique chemical structure allows it to be a key component in the development of new drugs, particularly those targeting specific biological pathways or receptors.
As a pharmaceutical intermediate, 2,4-DIOXO-1,2,3,4-TETRAHYDROPYRIMIDINE-5-SULFONYL CHLORIDE plays a vital role in the production of drugs that address a wide range of medical conditions. Its versatility in chemical reactions enables the creation of diverse drug candidates with potential applications in various therapeutic areas, such as oncology, cardiovascular diseases, and neurological disorders.

InChI:InChI=1/C4H3ClN2O4S/c5-12(10,11)2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)

Upstream product

• 66-22-8 uracil 

Downstream Products

• 90286-77-4 2,4-Dioxo-1,2,3,4-tetrahydro-pyrimidine-5-sulfonic acid o-tolylamide 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of N-phenyl-(2,4-dihydroxypyrimidine-5-sulfonamido)benzoyl hydrazide derivatives as thymidylate synthase (TS) inhibitors and as potential antitumor drugs

The Inhibition of cellular nucleotide metabolism to promote apoptosis is a key principle of cancer therapy. Thymidylate synthase (TS) is a key rate-limiting enzyme in the initiation of DNA synthesis in cell. Here, we presented two types of thymidylate synthase inhibitors, and, the key pharmacological properties of these two types of thymidylate synthase inhibitor were extracted and combined to design new compounds with inhibitory activity. Therefore, two series of 42 new compounds with the common biological effect of promoting apoptosis are designed and synthesized by combination principle. Most of the compounds had good anti-proliferative activity on A549, OVCAR-3, SGC7901 and MDA-MB-231 cells. The IC50 of compound 10l on A549 cells was 1.26 μM, which was better than that of pemetrexed (PTX, IC50 = 3.31 μM), furthermore, the selection index of compound 10l was higher than PTX. Flow cytometry analysis showed that compound 10l (the apoptosis rate is 39.4%) could induce A549 cell apoptosis and effectively inhibit tumor cell proliferation. Further western blot analysis showed that compound 10l could induce intrinsic apoptosis by activating caspase-3, increasing expression of cleaved caspase-3 and reducing the ratio of bcl-2/bax. All of this makes compound 10l to be a promising compound in future animal tumor models.

Design, synthesis and biological evaluation of novel uracil derivatives bearing 1, 2, 3-triazole moiety as thymidylate synthase (TS) inhibitors and as potential antitumor drugs

Research on thymidylate synthase inhibitors has been a hot spot for anticancer drug development. Here, based on the structures and pharmacological properties of two types of TS inhibitors, through a molecular assembly principle of drugs design, we designed and synthesized a series of 30 novel uracil derivatives as TS inhibitors. The antiproliferative ability of these compounds was evaluated against four cancer cell lines (A549, OVCAR-3, SGC-7901, and HepG2) by the MTT assay. Most of them showed excellent activities against all the tested cell lines. Furthermore, hTS assay results showed that these compounds have the unique ability to inhibit hTS activity in vitro. Notably, compound 13j exhibited the most potent activity against A549 cells (IC50 = 1.18 μM) and extremely prominent enzyme inhibition (IC50 = 0.13 μM), which was superior to the pemetrexed (PTX, IC50 = 3.29 μM and IC50 = 2.04 μM). Flow cytometric analysis showed the compound 13j could inhibit A549 cells proliferation by arresting the cell cycle in the G1/S phase, then induced the cell apoptosis. Further western blot analysis showed that compound 13j could down-regulate the cycle checkpoint proteins cyclin D1 and cyclin E to inhibit the cell cycle progression, and then induce intrinsic apoptosis by activating caspase-3, and reducing the ratio of bcl-2/bax. All of these results demonstrated that this new structure has potential drug-making properties and provides new ideas for drug development.

Pyrimidine-type antitumor compound, preparation method and application thereof

The invention belongs to the field of medicines and particularly relates to a pyrimidine-type antitumor compound, a preparation method and an application thereof. In the invention, the medicinal effect characters of a pyrimidine analogue and a TP inhibito

Pyrimidine type antitumor compounds having 1,3,4-oxadiazole structure and preparation method and application thereof

The invention belongs to the technical field of medicines, relates to compounds having antitumor activity and having specific chemical structures, and particularly relates to pyrimidine type antitumorcompounds having a 1,3,4-oxadiazole structure and a preparation method and application thereof. The general structure formula of the pyrimidine type antitumor compounds is shown as follows in the description. The novel compounds greatly improve antitumor effects, and have more excellent anti-proliferation capability for human lung cancer A549 cells when compared with pyrimidine acylhydrazine compounds. Synthetic steps are simplified in a synthesis process, thus making future industrial production possible.

Pyrimidine phenylurea anti-tumor compound and preparation method and application thereof

The invention belongs to the field of medicines, and particularly relates to a pyrimidine phenylurea anti-tumor compound and a preparation method and application thereof. A structure general formula of the pyrimidine phenylurea anti-tumor compound is spec

Uracil derivatives as inhibitors of TNF-alpha converting enzyme (TACE) and matrix metalloproteinases

The present application describes novel uracil derivatives of formula I: A-W-U-X-Y-Z-Ua-Xa-Ya-Za??I or pharmaceutically acceptable salt or prodrug forms thereof, wherein A, W, U, X, Y, Z, Ua, Xa, Ya, and Za are defined in the present specification, which are useful as inhibitors of TNF-α converting enzyme (TACE), matrix metalloproteinases (MMP), aggrecanase or a combination thereof.