Beziehungen zwischen algistatischer Aktivität und physikalisch-chemischen Eigenschaften von 5-Amino-1-aryl-1H-tetrazolen

Schelenz, Thomas

doi:10.1002/(sici)1521-3897(200002)342:2<205::aid-prac205>3.0.co;2-5

J. prakt. Chem.

2000

DOI: 10.1002/(sici)1521-3897(200002)342:2<205::aid-prac205>3.0.co;2-5

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Beziehungen zwischen algistatischer Aktivität und physikalisch-chemischen Eigenschaften von 5-Amino-1-aryl-1H-tetrazolen

Thomas Schelenz¹

Abstract: 205 5-Amino-1-aryl-1H-tetrazole verfügen mit muskelrelaxierenden und antiinflammatorischen [1,2], antiarthritischen, analgetischen und ulcustherapeutischen [3,4] sowie coccidiostatischen [5, 6] Eigenschaften über ein breites biologisches Wirkungsspektrum. Für isomere 5-Arylamino-1H-tetrazole und die unsubstituierte Leitstruktur 5-Amino-1H-tetrazol wurden darüber hinaus Abstract. A series of 20 5-amino-1-aryl-1H-tetrazoles was synthesized by diazotation of corresponding 1-amino-3-arylguanidines and tested for g… Show more

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Cited by 4 publications

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“…It is known that certain 5-amino-1-aryltetrazoles possess anti-inflammatory, myorelaxant, antiulcer, analgesic, and other biological activities [12]. It is known that certain 5-amino-1-aryltetrazoles possess anti-inflammatory, myorelaxant, antiulcer, analgesic, and other biological activities [12].…”

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Synthesis of New Functionally Substituted 1-R-tetrazoles and Their 5-Amino Derivatives

Войтехович

Vorob'ev

Гапоник

et al. 2005

Chem Heterocycl Compd

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Keywords: 1-R-5-aminotetrazoles, N-arylcyanamides, 1-R-tetrazoles.C-and N-tetrazolyl groups enter into the composition of a series of biologically active compounds, many of which are used in medicinal practice [1,2]. This is linked primarily with the unique structure of the tetrazole ring which, depending on the location of substituents, may be a bioisostere of a carboxyl or an amide grouping, possessing several advantages over them [2,3]. One of the most preferred routes for making a 1-monosubstituted tetrazole ring is the heterocyclization of primary amines with triethyl orthoformate and sodium azide [3]. This process is used for the synthesis of tetrazoles, starting from primary amines of various nature, including aliphatic, aromatic, and heterocyclic [4][5][6][7][8][9]. It was shown that the reaction proceeds smoothly with the participation of only the simplest alkyl and aryl amines. It was discovered that 2,4-dinitroaniline does not react [7], and in the case of ortho-phenylenediamine the process stops at the stage of forming benzimidazole, the condensation product of triethyl orthoformate with the initial amine [6]. Under analogous conditions thiosemicarbazide forms a 2-aminothiadiazole [7]. Conversion products of several other compounds with a primary amino group, including hydrazine, phenylhydrazine, melamine, and aminoguanidine, failed to be identified [7]. The behavior of other functionally substituted primary amines has not been studied up to the present time, in spite of the obvious effect of the nature of the substituent on the course of the heterocyclization reaction.In the development of these investigations and with the aim of broadening the preparative possibilities of this reaction, the heterocyclization of some alkyl-, aryl-, and hetarylamines has been studied in this work. These include substances of a series of widely known pharmaceutical preparations possessing antibacterial and antiviral action, comprising sulfanilamide, sulfaethidole, sulfadimidine, rimantadine, etc. It was discovered that primary amines 1 react with sodium azide and triethyl orthoformate in acetic acid at a molar ratio of reactants of 1:1.1:3, forming the corresponding 1-monosubstituted tetrazoles 2.

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confidence: 99%

Synthesis of New Functionally Substituted 1-R-tetrazoles and Their 5-Amino Derivatives

Войтехович

Vorob'ev

Гапоник

et al. 2005

Chem Heterocycl Compd

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Structure–activity analysis of harmful algae inhibition by congeneric compounds: case studies of fatty acids and thiazolidinediones

Huang

Xiao

Shi

et al. 2014

Environ Sci Pollut Res

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The occurrence of harmful algal blooms has been increasing significantly around the world. In order to ensure the safety of drinking water, procedures to screen potential materials as effective algicides are needed, and predictive methods which save both the labor and time compared with traditional experimental approaches, are particularly desirable. In this study, data from previous studies on the algal-growth inhibitory action of two kinds of compounds, namely, the action of fatty acids and thiazolidinediones on the harmful algae Heterosigma akashiwo and Chattonella marina, were modeled using multiple linear regression (MLR) based on quantitative structure-activity relationships (QSAR). The models were shown to have highly predictive ability and stability, and provided insight into the inhibitory mechanisms of congeneric compounds. The main descriptors in the fatty-acid models were the Connolly accessible area and the number of rotatable bonds, illustrating that molecular surface area and shape are important in their algicidal actions. In the thiazolidinedione models, the critical volume, octanol-water partition coefficient (LogP), and Connolly solvent-excluded volume were found to be significant, indicating that hydrophobicity, substituent group size, and mode of action are mechanistically important. Our results showed the algicidal activity of a series of compounds on different algae could be modeled, and each model is efficacious for compounds that fall into the application domain of the QSAR model. This work demonstrates how reliable predictions of the algicidal activity of novel compounds and explanations of their inhibitory mechanisms can be obtained.

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Copper(II), palladium(II) and platinum(II) chloride complexes with 5-amino-2-tert-butyltetrazole: Synthesis, characterization and cytotoxicity

et al. 2009

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Beziehungen zwischen algistatischer Aktivität und physikalisch-chemischen Eigenschaften von 5-Amino-1-aryl-1H-tetrazolen

Cited by 4 publications

References 15 publications

Synthesis of New Functionally Substituted 1-R-tetrazoles and Their 5-Amino Derivatives

Synthesis of New Functionally Substituted 1-R-tetrazoles and Their 5-Amino Derivatives

Structure–activity analysis of harmful algae inhibition by congeneric compounds: case studies of fatty acids and thiazolidinediones

Copper(II), palladium(II) and platinum(II) chloride complexes with 5-amino-2-tert-butyltetrazole: Synthesis, characterization and cytotoxicity

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