220429-71-0

Upstream product

• 4360-47-8 cinnamonitrile 
• 14371-10-9 (E)-3-phenylpropenal 
• 59336-59-3 cinnamaldehyde oxime 
• 1885-38-7 cinnamic nitrile 
• 20068-10-4 (E)-4-phenyl-3-butenenitrile 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 104-55-2 3-phenyl-propenal 
• 588-72-7 [(E)-2-bromoethenyl]benzene 

Downstream Products

• 1357019-55-6 1-[(3-methylphenyl)sulfonyl]-5-[(E)-2-phenylethenyl]-1H-tetrazole 
• 1357019-48-7 5-[(E)-2-phenylethenyl]-1-(phenylsulfonyl)-1H-tetrazole 
• 1357019-49-8 1-[(4-methylphenyl)sulfonyl]-5-[(E)-2-phenylethenyl]-1H-tetrazole 

Relevant academic research and scientific papers

Azole Based Acetohydrazide Derivatives of Cinnamaldehyde Target and Kill Candida albicans by Causing Cellular Apoptosis

Opportunistic fungal pathogens including Candida albicans are responsible for the alarming rise in hospital acquired infections and millions of deaths worldwide. The current treatment modalities are not enough to handle this situation, and therefore, new treatment modalities and strategies are desperately needed. In this direction, we synthesized a series of azole based acetohydrazide derivatives of cinnamaldehyde and subjected it to antifungal activity evaluation. Preliminary antifungal activity evaluation revealed tremendous antifungal potential of some of the derivatives against fluconazole susceptible and resistant clinical isolates of Candida albicans. Although all the compounds in the series are structurally similar except for the presence of different substituents on the phenyl ring of the acetohydrazide pendent, they sharply differed in their activity profile. Further mechanism of action studies revealed that these compounds have an apoptotic effect on C. albicans confirmed via Annexin V-FITC staining and TUNEL assay.

Efficient synthesis of tetrazole hemiaminal silyl ethers via three-component hemiaminal silylation

An efficient route to construct 2,5-disubstituted tetrazole hemiaminal silyl ethers via one-pot three-component hemiaminal silylation of 5-substituted tetrazoles, aldehydes, and silyl triflates was developed. Diverse 2,5-disubstituted tetrazole hemiaminal silyl ethers were obtained with 37?:?63->99?:?1 regioisomeric ratios. The regioselectivities of this reaction were significantly affected by steric hindrance and the conjugation effects of substitutions on the 5-position of tetrazoles.

Antibacterial assessment of heteroaryl, Vinyl, Benzyl, and Alkyl tetrazole compounds

Background: In previous reports, the antibacterial properties of certain tetrazole derivatives have been described. We have previously reported the antibacterial properties of aryl 1H-tetrazole compounds. Objective: To study the antibacterial activity of 5-substituted heteroaryl, vinyl, benzyl, and alkyl 1H-tetrazole derivatives. Methods: The antibacterial properties of heteroaryl, vinyl, benzylic, and aliphatic tetrazole derivatives were investigated against Escherichia coli, Staphylococcus aureus, and Pseudomonas aeruginosa. The activity was assessed by determining the minimum inhibitory concentration of these tetrazole derivatives and comparing them to the known antibiotics amoxicillin, trimethoprim and sulfamethoxazole. Results: The tetrazole compounds were prepared utilizing cerium(III) chloride heptahydrate catalysis at 160o C for 1-4 h in a microwave reactor using an aqueous solvent mixture. The most active derivatives exhibited minimum inhibitory concentration values between 125-250 μg/mL against Escherichia coli. More importantly, these compounds were considerably more active when used in combination with trimethoprim and a significant synergistic effect was observed (MIC = 0.98-7.81 μg/mL) against E. coli and S. aureus. Conclusion: The tetrazole derivatives were synthesized in high yield and short reaction times in water. Several of the tetrazole compounds showed a significant synergistic antibacterial effect when used with trimethoprim.

Cu(NO3)2-catalysed direct synthesis of 5-substituted 1H-tetrazoles from alcohols or aldehydes

A simple, convenient and practical protocol to synthesise 5-substituted 1H-tetrazoles from alcohols or aldehydes is reported. Using ammonia and sodium azide as nitrogen sources and Cu(NO3)2 as catalyst, benzylic alcohols and benzaldehydes were directly converted into 5-substituted 1H-tetrazoles in a one-pot procedure.

Design and synthesis of laser-activatable tetrazoles for a fast and fluorogenic red-emitting 1,3-dipolar cycloaddition reaction

The design and synthesis of a new class of laser light activatable tetrazoles with extended π-systems is reported. Upon 405 nm laser light irradiation, these bithiophene-substituted tetrazoles underwent extremely fast 1,3-dipolar cycloaddition reactions with dimethyl fumarate with second-order rate constants approaching 4000 M-1 s-1. The resulting pyrazoline cycloadducts exhibited solvent-dependent red fluorescence, making these tetrazoles potentially useful as fluorogenic probes for detecting alkenes in vivo.

One-step synthesis of 5-substituted 1 H -Tetrazoles from an aldehyde by reaction with acetohydroxamic acid and sodium azide under Bi(OTf)3 Catalysis

An efficient one-step method for the synthesis of 5-substituted 1H-tetrazoles from aldehydes by reaction with acetohydroxamic acid and sodium azide using bismuth(III) triflate as the catalyst is described. Georg Thieme Verlag Stuttgart · New York.

Proton-pumping-ATPase-targeted antifungal activity of cinnamaldehyde based sulfonyl tetrazoles

Azoles are generally fungistatic, and resistance to fluconazole is emerging in several fungal pathogens. We designed a series of cinnamaldehyde based sulfonyl tetrazole derivatives. To further explore the antifungal activity, in vitro studies were conduct

1,3-Dipolar cycloaddition: Click chemistry for the synthesis of 5-substituted tetrazoles from organoaluminum azides and nitriles

Cheap and safe: Conventional methods to prepare tetrazoles employ dangerous, toxic reagents. A new route to these heterocycles (see scheme) uses inexpensive and nontoxic dialkyl aluminum azides. The cycloaddition occurs under mild conditions and tolerates a variety of functional groups. The low cost and ecocompatibility make this process attractive for large-scale preparation. (Chemical Equation Presented).

PROCESS FOR THE PREPARATION OF TETRAZOLE DERIVATIVES FROM ORGANO BORON AND ORGANO ALUMINIUM AZIDES

The present invention relates to a method for preparing substituted tetrazoles, compounds obtained according to this method, new reactants and new tetrazole derivatives.

Preparation of 5-substituted 1H-tetrazoles from nitriles in water

The addition of sodium azide to nitriles to give 1H-tetrazoles is shown to proceed readily in water with zinc salts as catalysts. The scope of the reaction is quite broad; a variety of aromatic nitriles, activated and unactivated alkyl nitriles, substituted vinyl nitriles, thiocyanates, and cyanamides have all been shown to be viable substrates for this reaction.