59157-06-1

Basic information

• Product Name: 5,10-Dioxo-5H,10H-diimidazo(1,5-a:1,5-d)pyrazine-1,6-dicarbonyl dichloride
• Synonyms: 5,10-dioxo-5H,10H-diimidazo[1,5-a:1',5'-d]pyrazine-1,6-dicarboxylic acid dichloride;4H,9H-diimidazopyrazin 1,6-dicarbonyldichlorid;5,10-dioxo-5H,10H-diimidazo[1,5-a,1',5'-d]pyrazinedicarbonyl-1,6-dichloride;5,10-dioxo-5H,10H-diimidazo[1,5-a:1',5'-d]pyrazine-1,6-dicarbonyl dichloride;
• CAS NO: 59157-06-1
• Molecular Formula: C₁₀H₂Cl₂N₄O₄
• Molecular Weight: 313.056
• Mol File: 59157-06-1.mol

Chemical Properties

• Boiling Point: 729.7°Cat760mmHg
• Flash Point: 395.1°C
• Density: 2.13g/cm³
• CAS DataBase Reference: 5,10-Dioxo-5H,10H-diimidazo(1,5-a:1,5-d)pyrazine-1,6-dicarbonyl dichloride(CAS DataBase Reference)
• NIST Chemistry Reference: 5,10-Dioxo-5H,10H-diimidazo(1,5-a:1,5-d)pyrazine-1,6-dicarbonyl dichloride(59157-06-1)
• EPA Substance Registry System: 5,10-Dioxo-5H,10H-diimidazo(1,5-a:1,5-d)pyrazine-1,6-dicarbonyl dichloride(59157-06-1)

Safety Data

• Hazardous Substances Data: 59157-06-1(Hazardous Substances Data)

Upstream product

• 570-22-9 4,5-imidazoledicarboxylic acid 

Downstream Products

• 54296-21-8 2,2'-(1H-imidazole-4,5-diyl)bis(1H-benzo[d]imidazole) 

Relevant articles and documents

An inhibitor of fatty acid synthase thioesterase domain with improved cytotoxicity against breast cancer cells and stability in plasma

It is well recognized that many cancers are addicted to a constant supply of fatty acids (FAs) and exhibit brisk de novo FA synthesis. Upregulation of a key lipogenic enzyme, fatty acid synthase (FASN), is a near-universal feature of human cancers and their precursor lesions, and has been associated with chemoresistance, tumor metastasis, and diminished patient survival. FASN inhibition has been shown to be effective in killing cancer cells, but progress in the field has been hindered by off-target effects and poor pharmaceutical properties of candidate compounds. Our initial hit (compound 1) was identified from a high-throughput screening effort by the Sanford-Burnham Center for Chemical Genomics using purified FASN thioesterase (FASN-TE) domain. Despite being a potent inhibitor of purified FASN-TE, compound 1 proved highly unstable in mouse plasma and only weakly cytotoxic to breast cancer (BC) cells in vitro. An iterative process of synthesis, cytotoxicity testing, and plasma stability assessment was used to identify a new lead (compound 41). This lead is more cytotoxic against multiple BC cell lines than tetrahydro-4-methylene-2S-octyl-5-oxo-3R-furancarboxylic acid (the literature standard for inhibiting FASN), is stable in mouse plasma, and shows negligible cytotoxic effects against nontumorigenic mammary epithelial cells. Compound 41 also has drug-like physical properties based on Lipinski’s rules and is, therefore, a valuable new lead for targeting fatty acid synthesis to exploit the requirement of tumor cells for fatty acids.

AMIDO-SUBSTITUTED CYCLOHEXANE DERIVATIVES

The present invention relates to amido-substituted cyclohexane compounds of general formula (I) : in which m, A, R4, R6, R7, R8, R9, R10 and R11 are as defined herein, to methods of preparing said compounds, to intermediate compounds useful for preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds and to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, in particular of neoplasms, as a sole agent or in combination with other active ingredients.

AMIDO-SUBSTITUTED AZOLE COMPOUNDS

The present invention relates to compounds of general formula (I), in which X1, X2, R1, R2, R4, R5, R7, and R8 are as defined herein, to methods of preparing said compounds, to intermediate compounds useful for preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds and to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, in particular of neoplasms, as a sole agent or in combination with other active ingredients.

A class of 4, 5 - disubstituted imidazole derivatives and its preparation and use (by machine translation)

The invention relates to a compound of general formula I indicated by the 4, 5 - disubstituted imidazole compound, or its pharmaceutically acceptable salt, pharmaceutical composition containing the same and its preparation and use, the compounds can be used as a xanthine oxidase (Xanthine oxidase, XO) inhibitor, used for the treatment of uric acid crystallization at the joints to the deposition of Gout and its complications. (by machine translation)

AMIDO-SUBSTITUTED AZOLE COMPOUNDS

The present invention relates to amido-substituted azole compounds of general formula (I), in which X1, X2, R1, R2, R4, R5, R7 and R8 are as defined herein, to methods of preparing said compounds, to intermediate compounds useful for preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds and to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, in particular of neoplasms, as a sole agent or in combination with other active ingredients.

AMIDO-SUBSTITUTED CYCLOHEXANE DERIVATIVES

The present invention relates to amido-substituted cyclohexane compounds of general formula (I), in which A, R4, R6, R7, R8, R9, R10 and R11 are as defined herein, to methods of preparing said compounds, to intermediate compounds useful for preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds and to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, in particular of neoplasms, as a sole agent or in combination with other active ingredient.

AMIDO-SUBSTITUTED AZOLE COMPOUNDS

The present invention relates to amido-substituted azole compounds of general formula (I), in which X1, X2, R1, R2, R4, R5, R7 and R8 are as defined in the claims which are inhibitors of TNKS1 and/or TNKS2, to methods of preparing said compounds, to intermediate compounds useful for preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds and to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, in particular of neoplasms, as a sole agent or in combination with other active ingredients.

Synthesis and evaluation of imidazole-4,5-and pyrazine-2,3-dicarboxamides targeting dengue and yellow fever virus

The results of a high-throughput screening assay using the dengue virus-2 replicon showed that the imidazole 4,5-dicarboxamide (I45DC) derivative (15a) has a high dengue virus inhibitory activity. Based on 15a as a lead compound, a novel class of both disubstituted I45DCs and the resembling pyrazine 2,3-dicarboxamides (P23DCs) were synthesized. Here, we report on their in vitro inhibitory activity against dengue virus (DENV) and yellow fever virus (YFV). Some of these first generation compounds have shown activity against both viruses in the micromolar range. Within this series, compound 15b was observed to display the highest antiviral potency against YFV with an EC50 Combining double low line 1.85 μM. In addition, compounds 20a and 20b both potently inhibited replication of DENV (EC50 Combining double low line 0.93 μM) in Vero cells.

CYCLIC IMINOCARBAMATES AND USE THEREOF

The invention relates to novel cyclic iminocarbamates of formula (I), wherein R1, R2, R3, A, Z and n have the meaning cited in the description, to a method for the production thereof, to the use thereof for treating and/or for the prophylaxis of illnesses, and to the use thereof in the production of medicaments for treating and/or for the prophylaxis of diseases, in particular of thromboembolic diseases.

An improved method for the synthesis of dissymmetric N,N′-disubstituted imidazole-4,5-dicarboxamides

Symmetrically and dissymmetrically disubstituted imidazole-4,5-dicarboxamides (I45DCs) have diverse bioactivities and therefore represent useful small molecules for lead structure identification in drug discovery. For this reason, an improved synthesis was developed as a first step in the preparation of greater numbers of analogues. The method involves the transformation of imidazole-4,5-dicarboxylic acid into dissymmetrically disubstituted I45DCs in four steps and in a minimum yield of 51%. This reflects an overall reduction of one synthetic step and a greater than 30% improvement in yield over the known method.