1979-96-0

Basic information

• Product Name: 4,6-Dichloro-2-Methylsulfanyl-5-nitro-pyriMidine
• Synonyms: 4,6-Dichloro-2-Methylsulfanyl-5-nitro-pyriMidine;4,6-Dichloro-2-(Methylthio)-5-nitropyriMidine;2-Methylthio-4,6-dichloro-5-nitro-pyriMidine;4,6-Dichloro-2-Methylsulfanyl-5-nitro-pyriMidine-3
• CAS NO: 1979-96-0
• Molecular Formula: C₅H₃Cl₂N₃O₂S
• Molecular Weight: 240.06722
• Mol File: 1979-96-0.mol
• Article Data: 16

Chemical Properties

• Melting Point: 61 °C
• Boiling Point: 360.4°C at 760 mmHg
• Flash Point: 171.8°C
• Appearance: /
• Density: 1.7g/cm³
• Vapor Pressure: 4.61E-05mmHg at 25°C
• Refractive Index: 1.64
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -8.04±0.39(Predicted)
• CAS DataBase Reference: 4,6-Dichloro-2-Methylsulfanyl-5-nitro-pyriMidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6-Dichloro-2-Methylsulfanyl-5-nitro-pyriMidine(1979-96-0)
• EPA Substance Registry System: 4,6-Dichloro-2-Methylsulfanyl-5-nitro-pyriMidine(1979-96-0)

Safety Data

• Hazardous Substances Data: 1979-96-0(Hazardous Substances Data)

Usage

Description

4,6-Dichloro-2-Methylsulfanyl-5-nitro-pyriMidine, also known as 4,6-Dichloro-2-(methylthio)-5-nitro-pyrimidine, is a chemical compound with the molecular formula C5H3Cl2N3O2S. It is a synthetic intermediate that holds significant importance in the development of various pharmaceutical compounds. Its unique structure, which includes a pyrimidine ring with chlorine substitutions at the 4 and 6 positions, a methylthio group at the 2 position, and a nitro group at the 5 position, makes it a versatile building block in the synthesis of complex molecules.

Uses

Used in Pharmaceutical Industry:
4,6-Dichloro-2-Methylsulfanyl-5-nitro-pyriMidine is used as a synthetic intermediate for the development of Cathepsin K inhibition SAR (Structure-Activity Relationship). Cathepsin K is a cysteine protease enzyme that plays a crucial role in bone resorption, and its inhibition is a target for the treatment of osteoporosis and other bone-related disorders. 4,6-Dichloro-2-Methylsulfanyl-5-nitro-pyriMidine contributes to the understanding of the structure-activity relationship of Cathepsin K inhibitors, aiding in the design and synthesis of more potent and selective drugs.
Additionally, 4,6-Dichloro-2-Methylsulfanyl-5-nitro-pyriMidine is used in the synthesis of GS39783 (G797150), which is an allosteric positive modulator of GABAB receptors. GABAB receptors are metabotropic receptors that play a role in various physiological processes, including regulation of neurotransmitter release, modulation of neuronal excitability, and regulation of energy balance. Positive allosteric modulation of GABAB receptors has potential therapeutic applications in the treatment of neurological and psychiatric disorders, such as epilepsy, anxiety, and schizophrenia.

InChI:InChI=1/C5H3Cl2N3O2S/c1-13-5-8-3(6)2(10(11)12)4(7)9-5/h1H3

Upstream product

• 6632-63-9 6-chloro-2-(methylthio)pyrimidin-4-ol 
• 1979-98-2 4,6-dihydroxy-2-methylmercaptopyrimidine 
• 1979-97-1 2-(methylthio)-5-nitropyrimidine-4,6-diol 

Downstream Products

• 101622-51-9 olomoucine 
• 618863-11-9 4-(N,N-Benzylmethylamino)-6-(N-isopropylamino)-2-methylthio-5-nitropyrimidine 
• 136524-28-2 9-Ethyl-7-methyl-4-(dimethylamino)-2-(methylthio)imidazo[5,1-h]-pteridin-6(5H)-one 
• 56032-04-3 cyclohexyl-(2-methylsulfanyl-5-nitro-6-thiomorpholin-4-yl-pyrimidin-4-yl)-amine 
• 1337567-21-1 C₁₉H₁₉N₅O₄S 
• 1097966-93-2 4-(N-benzylamino)-6-chloro-2-methylthio-5-nitropyrimidine 

Relevant articles and documents

Discovery of 5-Nitro-6-thiocyanatopyrimidines as Inhibitors of Cryptococcus neoformans and Cryptococcus gattii

Opportunistic infections from pathogenic fungi present a major challenge to healthcare because of a very limited arsenal of antifungal drugs, an increasing population of immunosuppressed patients, and increased prevalence of resistant clinical strains due to overuse of the few available antifungals. Cryptococcal meningitis is a life-threatening opportunistic fungal infection caused by one of two species in the Cryptococcus genus, Cryptococcus neoformans and Cryptococcus gattii. Eighty percent of cryptococcosis diseases are caused by C. neoformans that is endemic in the environment. The standard of care is limited to old antifungals, and under a high standard of care, mortality remains between 10 and 30%. We have identified a series of 5-nitro-6-thiocyanatopyrimidine antifungal drug candidates using in vitro and computational machine learning approaches. These compounds can inhibit C. neoformans growth at submicromolar levels, are effective against fluconazole-resistant C. neoformans and a clinical strain of C. gattii, and are not antagonistic with currently approved antifungals.

Soluble guanylate cyclase stimulators for the treatment of hypertension: Discovery of MK-2947

The NO-sGC-cGMP signaling pathway plays an important role in the cardiovascular system. Loss of nitric oxide tone or impaired signaling has been associated with cardiovascular diseases, such as hypertension, pulmonary hypertension and heart failure. Direct activation of sGC enzyme independent of NO represents a novel approach for modulating NO signaling with tremendous therapeutic potential. Herein, we describe the design of a structurally novel class of heme-dependent sGC stimulators containing the 3,3-dimethylpyrrolidin-2-one moiety which resulted in the identification of the potent, selective stimulator 30 (MK-2947) for the treatment of hypertension.

PYRIMIDINE DERIVATIVES FOR PREVENTION AND TREATMENT OF BACTERIAL INFECTIONS

New pyrimidine derivatives of formula (I), optionally with a detectable isotope, pharmaceutical composition and method of preparation thereof. New pyrimidine derivatives for use in treatment or prevention of bacterial infection in a host mammal in need of such treatment or prevention and use as inhibitors of biofilm formation on a surface of biomaterial or medical device, particularly of cardiovascular device such as prosthetic heart valve or pacemakers. New pyrimidine derivatives for use as radiotracer in diagnosing or prognosing bacterial infection in a host mammal.