151291-05-3

Basic information

• Product Name: 3-AMINO-1-METHYL-5-(METHYLTHIO)-1H-PYRAZOLE-4-CARBONITRILE
• Synonyms: 3-AMINO-1-METHYL-5-(METHYLTHIO)-1H-PYRAZOLE-4-CARBONITRILE;1-Methyl-3-aMino-4-cyano-5-Methylsulfanylpyrazole;3-amino-1-methyl-5-(methylthio)-pyrazole-4-carbonitrile;1H-Pyrazole-4-carbonitrile,3-amino-1-methyl-5-(methylthio)-;1-Methyl-3-Amino-4-Cyano-5-Methylsulfanylpyrazole(WXC00844)
• CAS NO: 151291-05-3
• Molecular Formula: C₆H₈N₄S
• Molecular Weight: 168.22
• Mol File: 151291-05-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-AMINO-1-METHYL-5-(METHYLTHIO)-1H-PYRAZOLE-4-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AMINO-1-METHYL-5-(METHYLTHIO)-1H-PYRAZOLE-4-CARBONITRILE(151291-05-3)
• EPA Substance Registry System: 3-AMINO-1-METHYL-5-(METHYLTHIO)-1H-PYRAZOLE-4-CARBONITRILE(151291-05-3)

Safety Data

• Hazardous Substances Data: 151291-05-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
3-AMINO-1-METHYL-5-(METHYLTHIO)-1H-PYRAZOLE-4-CARBONITRILE is utilized as a key intermediate in the synthesis and design of potential drugs and bioactive compounds. Its structure and properties make it a valuable component for the development of therapeutic agents targeting various diseases.
Used in Organic Synthesis:
In the field of organic synthesis, 3-AMINO-1-METHYL-5-(METHYLTHIO)-1H-PYRAZOLE-4-CARBONITRILE is employed as a versatile building block for the creation of novel organic molecules. Its unique functional groups and reactivity allow for the formation of a wide range of chemical products.
Used in Materials Science:
3-AMINO-1-METHYL-5-(METHYLTHIO)-1H-PYRAZOLE-4-CARBONITRILE also finds applications in materials science, where its functional groups and reactivity can be harnessed to develop new materials with specific properties and applications.

Upstream product

• 5147-80-8 [Bis(methylthio)methylene]malononitrile 
• 60-34-4 methylhydrazine 
• 65889-71-6 3-(N²-benzylidene-N¹-methylhydrazino)-2-cyano-3-methylthioacrylonitrile 

Downstream Products

• 512846-20-7 1-(2-furan-2-yl-8-methyl-9-methylsulfanyl-8H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-yl)-3-(4-methoxy-phenyl)-urea 

Relevant articles and documents

Design, synthesis, and biological evaluation of C9- and C2-substituted pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines as new A2A and A3 adenosine receptors antagonists

In the past few years, our group has been involved in the development of A2A and A3 adenosine receptor antagonists which led to the synthesis of SCH58261 (5-amino-7-(2-phenylethyl)-2-(2-furyl)pyrazolo[4,3-e]-1,2,4-triazolo [1,5-c]pyrimidine, 61), potent and very selective at the A2A receptor subtype, and N8-substituted-pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c] pyrimidines-N5-urea or amide (MRE series, b), very selective at the human A3 adenosine receptor subtype. We now describe a large series of C9- and C2-substituted pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines to represent an extension of structure-activity relationship work on this class of tricyclic compounds. The introduction of a substituent at 9 position of the tricyclic antagonistic structure led to retention of receptor affinity but a loss of selectivity in respect to the lead compounds b, N8-substituted-pirazolo[4,3-e]-1,2,4-triazolo[1,5-c] pyrimidines-N5-urea or -amide. The substitution of the furanyl moiety of compound 61, necessary for receptor binding, with a phenyl or a substituted aromatic ring (compounds 5a-d, 6-8), caused a complete loss of the affinity at all the adenosine receptor subtypes, demonstrating that the furanyl ring is a necessary structural element to guarantee interaction with the adenosine receptor surface. The introduction of an ethoxy group at the ortho position of the aromatic ring to mimic the oxygen of the furan (compound 5c, 5-amino-7-(2-phenylethyl)-2-(2-ethoxyphenyl)pyrazolo[4,3-e]-1,2, 4-triazolo[1,5-c]pyrimidine) did not enhance affinity. The introduction of the cycloaminomethyl function by Mannich reaction at the 5′ position of the furanyl ring of 61 and the C9-substituted compound 41 (5-amino-8-methyl-9-methylsulfanyl-2-(2-furyl)-pyrazolo[4,3-e]-1,2, 4-triazolo[1,5-c]pyrimidine) resulted in complete water solubility but a loss of receptor affinity. We can conclude that modifications or substitutions at the furanyl ring are not allowed and the introduction of a substituent at the 9-position of the core pyrazolo-triazolo-pyrimidine structure caused a severe loss of selectivity, probably due to an increased steric hindrance of the radical introduced.

PHARMACEUTICALLY ACTIVE COMPOUNDS HAVING A TRICYCLIC PYRAZOLOTRIAZOLOPYRIMIDINE RING STRUCTURE AND METHODS OF USE

New compounds having a tricyclic pyrazolotriazolopyrimidine ring structure are provided and methods of using those compounds for a variety of therapeutic indications.

1-Methyl-5-alkylsulfonyl-, 1-methyl-5-alkylsulfinyl- and 1-methyl-5-alkylthio- substituted pyrazolylpyrazoles, processes for their preparation and their use as herbicides

1-Methyl-5-alkylsulfonyl-, 1-methyl-5-alkylsulfinyl- and 1-methyl-5-alkylthio-substituted pyrazolylpyrazoles, processes for their preparation and their use as herbicides 1 -Methyl-5-alkylsulfonyl-, 1-methyl-5-alkylsulfinyl- and 1-methyl-alkylthio-substitu

Substituted pyrazole derivatives

New substituted pyrazole derivatives of general formula I are described STR1 in which R1, R2, R3, R4, R5 and R6 have the meanings given in the description, processes for their preparation, as well as intermediates, and their use as herbicides.

Synthesis of Pyrrazoles and Pyrazolopyrimidines from 3-Arylsulfonylaminoacrylates

3-Arylsulfonylaminopyrazole-4-carboxamides and -carboxylates were synthesized from 3-arylsulfonylamino-3-methylthiocyanoacrylate derivatives as potential herbicidal inhibitors of the enzyme acetohydroxyacetic acid synthase (AHAS). Some of these compounds