149082-03-1

Usage

Uses

Used in Pharmaceutical Synthesis:
3,5-Dimethyl-2-hydroxymethyl-4-nitropyridine is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the formation of complex molecular structures that can exhibit therapeutic effects.
Used in Agricultural Chemicals:
In the agricultural sector, 3,5-Dimethyl-2-hydroxymethyl-4-nitropyridine is utilized as a precursor in the development of agrochemicals, potentially enhancing crop protection and yield through its incorporation into effective compounds.
Used in Organic Synthesis:
3,5-Dimethyl-2-hydroxymethyl-4-nitropyridine is employed as a building block in organic synthesis, allowing for the creation of a variety of complex organic molecules that can be tailored for specific applications in various industries.
Used in Chemical Research:
As a reagent, 3,5-Dimethyl-2-hydroxymethyl-4-nitropyridine is used in chemical research to explore its properties and reactions, contributing to the advancement of knowledge in organic chemistry and potentially leading to the discovery of new applications and compounds.
Used in Drug Development:
3,5-Dimethyl-2-hydroxymethyl-4-nitropyridine is utilized in the development of new drugs, capitalizing on its structural features to design molecules with potential therapeutic benefits in the treatment of various diseases and conditions.
Used in Agrochemical Development:
3,5-Dimethyl-2-hydroxymethyl-4-nitropyridine is also used in the development of agrochemicals, where its properties may be leveraged to create novel products that address specific needs in agriculture, such as pest control and crop enhancement.

InChI:InChI=1/C8H10N2O3/c1-5-3-9-7(4-11)6(2)8(5)10(12)13/h3,11H,4H2,1-2H3

Upstream product

• 695-98-7 2,3,5-trimethyl-pyridine 
• 74409-42-0 2,3,5-trimethylpyridine 1-oxide 
• 86604-79-7 2,3,5-trimethyl-4-nitropyridine N-oxide 
• 142885-95-8 2-acetyloxymethyl-3,5-dimethyl-4-nitropyridine 

Downstream Products

• 368890-24-8 (3,5-dimethyl-4-nitropyridin-2-yl)methyl 4-methylbenzenesulfonate 

Relevant academic research and scientific papers

Improved synthetic approach to tenatoprazole

An improved synthetic approach to tenatoprazole 1 is described. It started from 2,3,5-trimethyl-4-nitropyridine-N-oxide 2 with acetic anhydride via rearrangement and hydrolysis to give 3, Chlorination with SOCl2 yielded 2-chloromethyl-3,5-dimethyl-4-nitropyridine hydrochloride 4, then 4 condensed with 2-mercapto-5-methoxy imidazole [4,5-b]pyridine 5 to give 5-methoxy-2-[(4-nitro-3,5-dimethyl-2-pyridinyl)methylthio]imidazole[4,5-b] pyridine 6. At last the title compound 1 was produced by two methods: 6 was oxidized with MCPBA and then methoxylated with CH3ONa to give 1 and 6 was first methoxylated with CH3ONa and then oxidized with MCPBA to give 1. The overall yield is around 26% for both five-step syntheses. Copyright Taylor & Francis Group, LLC.

Rationally designed high-affinity 2-amino-6-halopurine heat shock protein 90 inhibitors that exhibit potent antitumor activity

Heat shock protein 90 (Hsp90) is a molecular chaperone protein implicated in stabilizing the conformation and maintaining the function of many cell-signaling proteins. Many oncogenic proteins are more dependent on Hsp90 in maintaining their conformation, stability, and maturation than their normal counterparts. Furthermore, recent data show that Hsp90 exists in an activated form in malignant cells but in a latent inactive form in normal tissues, suggesting that inhibitors selective for the activated form could provide a high therapeutic index. Hence, Hsp90 is emerging as an exciting new target for the treatment of cancer. We now report on a novel series of 2-amino-6-halopurine Hsp90 inhibitors exemplified by 2-amino-6-chloro-9-(4-iodo-3,5-dimethylpyridin- 2-ylmethyl)purine (30). These highly potent inhibitors (IC50 of 30 = 0.009 μM in a HER-2 degradation assay) also display excellent antiproliferative activity against various tumor cell lines (IC50 of 30 = 0.03 μM in MCF7 cells). Moreover, this class of inhibitors shows higher affinity for the activated form of Hsp90 compared to our earlier 8-sulfanylpurine Hsp90 inhibitor series. When administered orally to mice, these compounds exhibited potent tumor growth inhibition (>80%) in an N87 xenograft model, similar to that observed with 17-allylamino-17- desmethoxygeldanamycin (17-AAG), which is a compound currently in phase I/II clinical trials.

Intermediates and an improved process for the preparation of Omeprazole employing the said intermediates

This invention relates to an improved process for the preparation of Omeprazole of the formula-I starting from 4-nitro-2,3,5-trimethylpyridine-N-oxide and through novel intermediates 2-hydroxymethyl-3,5-dimethyl-4-nitro pyridine of the formula II and novel 2-chloromethyl-3,5-dimethyl-4-nitro pyridine of the formula III. This invention also relates to processes for the preparation of the above said novel intermediates. Omeprazole is one of the world's widely used drugs for the treatment of ulcer diseases. This compound acts by irreversible inhibition of the H+K+ATPase enzyme, which is part of the proton pump located in the parietal cell of the stomach wall.

Synthetic procedure for 5-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methylthio]-IH-benzimidazole hydrochloride and its conversion to omeprazole

The present invention relates to an efficient process for the preparation of 5-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methylthio]-1-H-benzimidazole hydrochloride starting from 3,5-Lutidine and its conversion to Omeprazole (5-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methylsulfinyl]-1H-benzimidazole) by selective oxidation with hydrogen peroxide.