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Usage

Uses

Used in Synthetic Chemistry:
5-(chloromethyl)-3-(2-methylphenyl)-1,2,4-oxadiazole is used as a synthetic intermediate for the preparation of various complex organic molecules. Its unique structure, featuring the oxadiazole ring and substituents, makes it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Research Applications:
5-(chloromethyl)-3-(2-methylphenyl)-1,2,4-oxadiazole is employed as a research compound in the study of chemical reactivity and the development of new synthetic methodologies. Its reactivity can be explored in various chemical reactions, such as nucleophilic substitutions, electrophilic aromatic substitutions, and cycloadditions, to generate novel compounds with potential applications in various fields.
Used in Pharmaceutical Development:
Although there is limited information on its direct use in pharmaceuticals, 5-(chloromethyl)-3-(2-methylphenyl)-1,2,4-oxadiazole may serve as a key intermediate in the synthesis of drug candidates. Its structural features could be exploited to design new molecules with improved pharmacological properties, such as increased potency, selectivity, or bioavailability.
Used in Material Science:
5-(chloromethyl)-3-(2-methylphenyl)-1,2,4-oxadiazole could be utilized in the development of new materials with unique properties, such as high thermal stability, chemical resistance, or specific optical characteristics. Its incorporation into polymers or other materials may lead to the creation of advanced materials for various industrial applications, including electronics, coatings, or adhesives.

InChI:InChI=1/C10H9ClN2O/c1-7-4-2-3-5-8(7)10-12-9(6-11)14-13-10/h2-5H,6H2,1H3

Upstream product

• 111457-51-3 C₁₀H₁₁ClN₂O₂ 
• 40312-14-9 (Z)-N'-hydroxy-2-methylbenzamidine 
• 40312-14-9 N'-hydroxy-2-methylbenzamidine 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 110722-45-7 [4-Oxo-3-(3-o-tolyl-[1,2,4]oxadiazol-5-ylmethyl)-3,4-dihydro-phthalazin-1-yl]-acetic acid 
• 1012283-22-5 3-o-tolyl-5-{(5-(3-o-tolyl-1,2,4-oxadiazol-5-yl)methylthio)-(1,3,4-thiadiazol-2-ylthio)methyl}-1,2,4-oxadiazole 

Relevant academic research and scientific papers

One-potCuAAC synthesis of (1H-1,2,3-triazol-1-yl)methyl-1,3,4/1,2,4-oxadiazoles starting from available chloromethyl-1,3,4/1,2,4-oxadiazoles

The one-pot CuAAC synthesis of (1H-1,2,3-triazol-1-yl)methyl-1,3,4-oxadiazole and (1H-1,2,3-triazol-1-yl)methyl-1,2,4-oxadiazole derivatives via three-component reaction of consequent nucleophilic substitution of chlorine, with azide, and its further “cli

The discovery of a selective, high affinity A2B adenosine receptor antagonist for the potential treatment of asthma

Adenosine has been suggested to play a role in asthma, possibly via activation of A2B adenosine receptors on mast cells and other pulmonary cells. We describe our initial efforts to discover a xanthine based selective A2B AdoR antagonist that resulted in the discovery of CVT-5440, a high affinity A2B AdoR antagonist with good selectivity (A2B AdoR Ki = 50 nM, selectivity A1 > 200: A2A > 200: A3 > 167).

NEW COMPOUNDS

The present invention relates to new compounds of formula I, (I) a process for their preparation and new intermediates prepared therein, pharmaceutical formulations containing said compounds and to the use of said compounds in therapy.

Potent, orally active aldose reductase inhibitors related to zopolrestat: Surrogates for benzothiazole side chain

A broad structure-activity program was undertaken in search of effective surrogates for the key benzothiazole side chain of the potent aldose reductase inhibitor, zopolrestat (1). A structure-driven approach was pursued, which spanned exploration of three areas: (1) 5/6 fused heterocycles such as benzoxazole, benzothiophene, benzofuran, and imidazopyridine; (2) 5- membered heterocycles, including oxadiazole, oxazole, thiazole, and thiadiazole, with pendant aryl groups, and (3) thioanilide as a formal equivalent of benzothiazole. Several benzoxazole- and 1,2,4-oxadiazole- derived analogues were found to be potent inhibitors of aldose reductase from human placenta and were orally active in preventing sorbitol accumulation in rat sciatic nerve, in an acute test of diabetic complications. 3,4-Dihydro-4- oxo-3-[(5,7-difluoro-2-benzoxazolyl)methyl]-1-phthalazineacetic acid (124) was the best of the benzoxazole series (IC50 = 3.2 x 10-9 M); it suppressed accumulation of sorbitol in rat sciatic nerve by 78% at an oral dose of 10 mg/kg. Compound 139, 3,4-dihydro-4-oxo-3-[[(2-fluorophenyl)-1,2,4- oxadiazol-5-yl]methyl]-1-phthalazineacetic acid, with IC50 -8 M, caused a 69% reduction in sorbitol accumulation in rat sciatic nerve at an oral dose of 25 mg/kg. The thioanilide side chain featured in 3-[2-[[3- (trifluoromethyl)phenyl]amino]-2-thioxoethyl]-3,4-dihydro-4-oxo-1- phthalazineacetic acid (195) proved to be an effective surrogate for benzothiazole. Compound 195 was highly potent in vitro (IC50 = 5.2 x 10-8 M) but did not show oral activity when tested at 100 mg/kg. Additional structure-activity relationships encompassing a variety of heterocyclic side chains are discussed.

REACTION OF AMIDOXIMES WITH α-CHLOROACID CHLORIDES: NOVEL SYNTHESIS OF 1,2,4-OXADIAZIN-5-ONES

The reaction of amidoximes with α-chloroacid chlorides gives under thermal reaction conditions 5-(1-chloroalkyl)-1,2,4-oxadiazoles.In presence of a strong base, the reaction follows a different path leading to the formation of 4H-1,2,4-oxadiazin-5(6H)-one