Computer Aided Benzothiazole Derivatives. Synthesis, Structure and Biological Study of New Push-Pull Conjugated Benzothiazolium Salts

Buffa, Radovan; Zahradnı́k, Pavol; Foltínová, P

doi:10.1515/hc.2001.7.4.331

Cited by 16 publications

(9 citation statements)

References 3 publications

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“…1, Scheme 5), a red fluorescent dye derived from reported push-pull conjugated benzothiazolium compounds. 24 The used dyes are relatively low molecular weight compounds (300-400 g/mol), and are therefore anticipated to be well suited for the construction of fluorescent antagonists from small GPCR ligands. The resulting fluorescent pyridinium compounds can be excited with the 488 nm argon laser and UR-DE99 derivatives are suited for excitation with a red diode laser (635 nm).…”

Section: Chemistrymentioning

confidence: 99%

“…Except for 40 these compounds were prepared by coupling of the corresponding Nprotected (Boc, Cbz) x-aminocarboxylic acids (16,17,19,23,24,28,35) to building block 12 or 30 (synthesis described previously) 6 with the aid of 1,1 0 -carbonyldiimidazole (CDI) (Scheme 3). The protected intermediates were purified by column chromatography prior to Boc-or Cbz-deprotection yielding the amines.…”

Section: Chemistrymentioning

confidence: 99%

“…24 N-Alkylation of benzothiazole 48 with methyl 4-bromobutanoate using the latter as solvent gave N-alkylated benzothiazolium derivative 49. Condensation of acrylic aldehyde 47 with benzothiazolium derivative 49 yielded methyl ester 50, 24 which was hydrolysed to the carboxylic acid 51 using lithium hydroxide.…”

Section: Chemistrymentioning

confidence: 99%

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Red-fluorescent argininamide-type NPY Y1 receptor antagonists as pharmacological tools

Keller

Erdmann

Pop

et al. 2011

Bioorganic & Medicinal Chemistry

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Section: Chemistrymentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

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Red-fluorescent argininamide-type NPY Y1 receptor antagonists as pharmacological tools

Keller

Erdmann

Pop

et al. 2011

Bioorganic & Medicinal Chemistry

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“…Many of 2-R substituted benzothiazoles are known as substances with antibacterial and antifungal activities (Foltínová et al 1978, Grandolini et al 1986, Afsah and Nayer 1996 and are reported also to be active as antineoplastics (Krieg and Bilitz 1996) agent. The newly synthesized 2-R substituted benzothiazole compounds were tested under in vitro conditions and some of them exhibited antimicrobial activity against Euglena gracilis and gram-positive bacteria as Staphylococcus aureus and Bacillus subtilis (Magdolen et al 2000a, Buffa et al 2001. However, none of them have been reported to have plant growth regulation activity.…”

mentioning

confidence: 99%

Benzothiazole derivatives substituted in position 2 as biologically active substances with plant growth regulation activity

Šimonová¹,

Henselová²,

Zahradnı́k³

2005

PLANT SOIL ENVIRON

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Thirteen of the new synthetized 2-R substituted benzothiazole derivatives have been tested for plant growth regulatory (PGR) activity. The effect on growth elongation was studied on wheat coleoptile segments Triticum aestivum L. cv. Blava, and on the hypocotyl and roots in cucumber Cucumis sativum L. cv. Evita. The formation and number of adventitious roots and the length of hypocotyl in Vigna radiata (L.) Wilczek and, the effect on the length of stem, fresh and dry mass in buckwheat Fagopyrum esculentum Moench. cv. Pyra were evaluated. Cytokinin activity was determined on segments of barley leaves Hordeum vulgare L. cv. Jubilant on the basis of senescence inhibition and chlorophyll content. The benzothiazole derivatives were tested in the range of 10<sup>–3</sup>–10<sup>–7</sup>M concentrations, and PGR activity was compared with indole-3-acetic acid, indole-3-butyric acid and 6-furfurylaminopurine. All tested derivatives showed different auxine-like effects on elongation growth of plants and the stimulative effects were found to depend on applicable concentrations. At higher concentration rates, derivatives acted as growth retardants and inhibited the length of cucumber hypocotyl and roots. The derivatives increased the formation of adventitious roots of mung bean hypocotyl cuttings, as well as stem elongation and production of fresh and dry mass of buckwheat. Cytokinin activity was confirmed in one derivate only with a significant effect on the inhibition of leaf senescence and higher chlorophyll content. The tested benzothiazole derivatives may be characterized as biologically active substances with dominant auxine-like growth promoting activity

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“…2,3,5-Trialkylbenzothiazolium salts 1 were prepared according to literature [6][7][8] . The reaction was performed either in nitromethane (R 2 = methyl or prop-2-yn-1-yl) or without solvent in an autoclave (R 2 = allyl).…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and QSAR Studies of New Conjugated Benzothiazole Derivatives

Buffa¹,

Zahradnı́k²,

Foltínová³

2002

Collect. Czech. Chem. Commun.

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Computer Aided Benzothiazole Derivatives. Synthesis, Structure and Biological Study of New Push-Pull Conjugated Benzothiazolium Salts

Cited by 16 publications

References 3 publications

Red-fluorescent argininamide-type NPY Y1 receptor antagonists as pharmacological tools

Red-fluorescent argininamide-type NPY Y1 receptor antagonists as pharmacological tools

Benzothiazole derivatives substituted in position 2 as biologically active substances with plant growth regulation activity

Synthesis and QSAR Studies of New Conjugated Benzothiazole Derivatives

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