57846-83-0

Basic information

• Product Name: (5-IODO-2,4-DIOXO-3,4-DIHYDRO-2H-PYRIMIDIN-1-YL)-ACETIC ACID
• Synonyms: (5-IODO-2,4-DIOXO-3,4-DIHYDRO-2H-PYRIMIDIN-1-YL)-ACETIC ACID;CHEMBRDG-BB 5727846;(5-IODO-2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)ACETIC ACID
• CAS NO: 57846-83-0
• Molecular Formula: C₆H₅IN₂O₄
• Molecular Weight: 296.02
• Mol File: 57846-83-0.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (5-IODO-2,4-DIOXO-3,4-DIHYDRO-2H-PYRIMIDIN-1-YL)-ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (5-IODO-2,4-DIOXO-3,4-DIHYDRO-2H-PYRIMIDIN-1-YL)-ACETIC ACID(57846-83-0)
• EPA Substance Registry System: (5-IODO-2,4-DIOXO-3,4-DIHYDRO-2H-PYRIMIDIN-1-YL)-ACETIC ACID(57846-83-0)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 57846-83-0(Hazardous Substances Data)

Usage

Description

(5-IODO-2,4-DIOXO-3,4-DIHYDRO-2H-PYRIMIDIN-1-YL)-ACETIC ACID is a pyrimidine derivative that serves as a potential intermediate in the synthesis of pharmaceutical compounds. Its structure features an iodo group and a dioxo moiety, which suggest its utility in organic synthesis and medicinal chemistry.
Used in Pharmaceutical Industry:
(5-IODO-2,4-DIOXO-3,4-DIHYDRO-2H-PYRIMIDIN-1-YL)-ACETIC ACID is used as a chemical intermediate for the development of novel drugs, leveraging its unique structural features to contribute to the creation of new pharmaceutical agents.
Used in Organic Synthesis:
(5-IODO-2,4-DIOXO-3,4-DIHYDRO-2H-PYRIMIDIN-1-YL)-ACETIC ACID is used as a building block in the synthesis of complex organic molecules, taking advantage of its reactive functional groups to facilitate the formation of desired compounds.

Upstream product

• 696-07-1 5-iodouracil 
• 79-08-3 bromoacetic acid 
• 213454-72-9 methyl 2-(5-iodo-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetate 
• 207724-94-5 N¹-(tert-butoxycarbonylmethyl)-5-iodouracil 
• 79-11-8 chloroacetic acid 

Downstream Products

• 668474-58-6 [(2-tert-butoxycarbonylamino-ethyl)-({5-[3-(4,5-dimethoxy-2-nitro-benzyloxycarbonylamino)-prop-1-ynyl]-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl}-acetyl)-amino]-acetic acid ethyl ester 
• 431042-68-1 [(2-tert-butoxycarbonylamino-ethyl)-({5-[3-(4-methoxy-benzylsulfanyl)-prop-1-ynyl]-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl}-acetyl)-amino]-acetic acid ethyl ester 

Relevant articles and documents

Conjugation and evaluation of small hydrophobic molecules to triazole-linked siRNAs

Short interfering RNAs (siRNAs) have tremendous potential as a new class of next-generation therapeutics; however, their progress is lagging due to issues related to stability, biodistribution, and cell-membrane permeability. To overcome these issues, there is widespread interest in chemically modifying siRNAs. In this study, siRNAs that contain a triazole-backbone unit with pyrimidine-modified hydrophobic substituents were synthesized and examined for their gene-silencing activity. In our study, we generated a library of siRNAs that target both a plasmid reporter system and an endogenous gene target, bcl-2. Our results indicate that these unique modifications are well tolerated within the RNA interference pathway. In addition, a cholesterol-modified triazole-linked siRNA targeting the exogenous target firefly luciferase was capable of gene-silencing at levels greater than 80% in the absence of a carrier complex.

Synthesis and antitumor activity of novel substituted uracil-1′(N)-acetic acid ester derivatives of 20(S)-camptothecins

A series of novel substituted uracil-1′(N)-acetic acid esters (6–20) of camptothecins (CPTs) were synthesized by the acylation method. These new compounds were evaluated for in vitro antitumor activity against tumor cell lines, A549, Bel7402, BGC-823, HCT-8 and A2780. In vitro results showed that most of the derivatives exhibited comparable or superior cytotoxicity compare to CPT (1) and topotecan (TPT, 2), with 12 and 13 possessing the best efficacy. Four compounds, 9, 12, 13 and 16, were selected to be evaluated for in vivo antitumor activity against H22, BGC-823 and Bel-7402 in mice. In vivo testing results indicated that 12 and 13 had antitumor activity against mouse liver carcinoma H22close to Paclitaxel and cyclophosphamide. 12 had similar antitumor activity against human gastric carcinoma BGC-823 in nude mice compared to irinotecan (3) and possessed better antitumor activity against human hepatocarcinoma Bel-7402 in nude mice than 2. It is also discovered that 12 showed a similar mechanism but better inhibitory activity on topoisomerase I (Topo I) compared to 2. These findings indicate that 20(S)-O-fluorouracil-1′(N)-acetic acid ester derivative of CPTs, 12, could be developed as an antitumor drug candidate for clinical trial.

C(5) modified uracil derivatives showing antiproliferative and erythroid differentiation inducing activities on human chronic myelogenous leukemia K562 cells

The K562 cell line has been proposed as a useful experimental system to identify anti-tumor compounds acting by inducing terminal erythroid differentiation. K562 cells exhibit a low proportion of hemoglobin-synthesizing cells under standard cell growth conditions, but are able to undergo terminal erythroid differentiation when treated with a variety of anti-tumor compounds. In this paper we report a screening study on a set of different modified C(5) uracil derivatives for the evaluation of their antiproliferative effect in connection with erythroid differentiation pathways, and for defining a new class of drug candidates for the treatment of chronic myelogenous leukemia. Activity of the derivatives tested can be classified in two effect: an antiproliferative effect linked to a high level of erythroid differentiation activity and an antiproliferative effect without activation of gamma globin genes The highest antiproliferative effect and erythroid induction was shown by compound 9, a thymine derivative bearing a n-octyl chain on nitrogen N(1), whereas thymine did not show any effect, suggesting the importance of the linear alkyl chain in position N(1). To our knowledge this compound should be considered among the most efficient inducers of erythroid differentiation of K562 cells. This work is the starting point for the quest of more effective and specific drugs for the induction of terminal erythroid differentiation, for leading new insights in the treatment of neoplastic diseases with molecules acting by inducing differentiation rather than by simply exerting cytotoxic effects.