143208-55-3

Basic information

• Product Name: 5-(benzo[d][1,3]dioxol-5-ylmethylene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione
• Synonyms: 5-(benzo[d][1,3]dioxol-5-ylmethylene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione;5-Benzo[1,3]dioxol-5-ylmethylene-1,3-dimethyl-pyrimidine-2,4,6-trione
• CAS NO: 143208-55-3
• Molecular Formula: C₁₄H₁₂N₂O₅
• Molecular Weight: 288.25548
• Mol File: 143208-55-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-(benzo[d][1,3]dioxol-5-ylmethylene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(benzo[d][1,3]dioxol-5-ylmethylene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione(143208-55-3)
• EPA Substance Registry System: 5-(benzo[d][1,3]dioxol-5-ylmethylene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione(143208-55-3)

Safety Data

• Hazardous Substances Data: 143208-55-3(Hazardous Substances Data)

Upstream product

• 120-57-0 piperonal 
• 769-42-6 1,3-dimethylbarbituric acid 
• 6642-31-5 6-Amino-1,3-dimethylbarbituric acid 

Downstream Products

• 143208-54-2 5-Benzo[1,3]dioxol-5-yl-1,3-dimethyl-6-phenylamino-1H-furo[2,3-d]pyrimidine-2,4-dione 

Relevant articles and documents

Leucettamine B analogs and their carborane derivative as potential anti-cancer agents: Design, synthesis, and biological evaluation

Leucettamine B is a natural product found in marine sponge Leucetta microraphis. Several of analogs of its family, such as aplysinopsine and clathridine, are medicinally active molecules which have applications in many pharmaceuticals and healthcare products; however, thus far, leucettamine B has not been studied. In this report, we describe the synthesis of a new class of analogs of leucettamine B obtained by Knoevenagel condensation using a microwave reactor. The 25 newly synthesized compounds were tested against MDA-MB-468, SW480, and Mahlavu cell lines for anticancer activity. Among them, the carborane-based compound (Z)-5-(benzo[d][1,3]dioxol-5-ylmethylene)-3-(1-closo-carboranyl)-2-thioxo -thiazolidin-4-one (49) and (Z)-5-(benzo[d][1,3]dioxol-5-ylmethylene)-3-(2-(pyrrolidin-1-yl)ethyl)-2-thioxothiazolidin-4-one (31) derivatives were found to have the most potential for use against tumor cells. The carborane derivative 49 had the lowest IC50 value against the SW480 cell line (4.7 μM) and the Mahlavu (6.6 μM) cell line. Furthermore, compound 31 also had a low IC50 value against SW480 (7.5 μM). Our research shows that leucettamine B analogs might have potential for use in cancer chemotherapy.

Synthesis of spirobarbiturate-pyrrolidinones: Via a domino aza-Michael/SN2 cyclization of barbiturate-derived alkenes with N-alkoxy α-haloamides

A highly efficient domino aza-MIRC (Michael Induced Ring Closure) reaction between barbiturate-derived alkenes and N-alkoxy α-haloamides has been achieved in moderate to excellent yields. This reaction proceeds smoothly under mild conditions via a domino aza-Michael addition/intramolecular SN2 sequence, providing a practical tool in the synthesis of bioactive molecules spirobarbiturate-3-pyrrolidinones.

SHIKIMATE PATHWAY INHIBITORS AND THE USE THEREOF

The present invention relates to methods of inhibiting shikimate pathway, comprising administering to a subject a pharmaceutically acceptable composition comprising a compound having a formula: or pharmaceutically acceptable salts thereof. The present invention also provides a synergistic antibacterial composition containing compound

A facile and clean synthesis of pyrimidine derivatives via three-component reaction in aqueous Media

A series of 5-benzylidenepyrimidine-2,4,6(1H,3H,5H)-trione and 5,5'-(arylmethylene) bis[6-aminopyrimidine-2,4(1H,3H)-dione] derivatives were synthesized via the three-component reactions of aromatic aldehyde, 6-aminopyrimidine-2,4-dione and Medrum's acid in aqueous media in the presence of triethylbenzylammonium chloride. The structures of the products were affected by substituents of aromatic aldehydes.

SYNTHESIS OF 6-PHENYLAMINOFUROPYRIMIDINE-2,4(1H,3H>-DIONES FROM BARBITURYLBENZYLIDENES AND ISONITRILES

Barbiturylbenzylidenes, prepared by Perkin condensation of aromatic aldehydes with 1,3-dimethylbarbituric acid, react with phenylisonitrile to yield four 5-aryl-6-phenylamino-1,3-dimethylfuropyrimidine-2,4(1H,3H)-diones.