New Naphthalene Derivatives with Liquid Crystalline Glassy States

Schäfer, Wolfgang; Uhlig, Gabriele; Zaschke, H.; Demus, D.; Diele, Siegmar; Kresse, H.; Ernst, S.; Wedler, W.

doi:10.1080/00268949008038604

Cited by 13 publications

(2 citation statements)

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“…The purity for all compounds was established to be ≥95% by HPLC, 1 H NMR, and 13 C NMR, unless otherwise stated. Acyl chloride precursors of β-keto esters 11a – d − are known compounds. The synthetic preparation and spectroscopic data of catechol pyrazolinone 8a have previously been published in a patent…”

Section: Methodsmentioning

confidence: 99%

Catechol Pyrazolinones as Trypanocidals: Fragment-Based Design, Synthesis, and Pharmacological Evaluation of Nanomolar Inhibitors of Trypanosomal Phosphodiesterase B1

Orrling¹,

Jansen

et al. 2012

J. Med. Chem.

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Trypanosomal phosphodiesterases B1 and B2 (TbrPDEB1 and TbrPDEB2) play an important role in the life cycle of Trypanosoma brucei, the causative parasite of human African trypanosomiasis (HAT), also known as African sleeping sickness. We used homology modeling and docking studies to guide fragment growing into the parasite-specific P-pocket in the enzyme binding site. The resulting catechol pyrazolinones act as potent TbrPDEB1 inhibitors with IC₅₀ values down to 49 nM. The compounds also block parasite proliferation (e.g., VUF13525 (20b): T. brucei rhodesiense IC₅₀ = 60 nM, T. brucei brucei IC₅₀ = 520 nM, T. cruzi = 7.6 μM), inducing a typical multiple nuclei and kinetoplast phenotype without being generally cytotoxic. The mode of action of 20b was investigated with recombinantly engineered trypanosomes expressing a cAMP-sensitive FRET sensor, confirming a dose-response related increase of intracellular cAMP levels in trypanosomes. Our findings further validate the TbrPDEB family as antitrypanosomal target.

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Section: Methodsmentioning

confidence: 99%

Catechol Pyrazolinones as Trypanocidals: Fragment-Based Design, Synthesis, and Pharmacological Evaluation of Nanomolar Inhibitors of Trypanosomal Phosphodiesterase B1

Orrling¹,

Jansen

et al. 2012

J. Med. Chem.

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show abstract

“…The presence of more than two aromatic rings in the molecular further increases A x above the biphenyl values. SQUID measurements of a four-component nematic mixture (E2) [47] containing naphthyl and phenyl groups have been performed by Turk [ 191. Figure 1 shows the composition of the sample, which provides an extended nematic range when supercooled in a glassy state. The mass susceptibility anisotropy of the mixture as a function of temperature is shown in Fig.…”

Section: Experimental Datamentioning

confidence: 99%

Nematic Liquid Crystals: Physical Properties, Section 2.3

Stannarius¹,

Demus²,

Goodby

et al. 1998

Handbook of Liquid Crystals

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Common nematic liquid crystals represent diamagnetic fluids. Molecular diamagnetism in non-ordered isotropic materials in general, as well as the mean diamagnetic polarizability in ordered materials, is temperature independent. However, due to thermal expansion of the material the volume susceptibility x is not constant but decreases with increasing temperature.' It is therefore sometimes convenient to introduce the temperature independent quantities x'~', the susceptibility per mole, or x (~) , the mass susceptibility, which are related to x by x (~) = M,X/p (m3 mol-'1 and X(m) = X I P (m3 kg -') where M,,, is the molar mass of the substance and p is the mass density.

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Diamagnetic Properties of Nematic Liquid Crystals

Stannarius¹

1998

Handbook of Liquid Crystals Set

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New Naphthalene Derivatives with Liquid Crystalline Glassy States

Cited by 13 publications

References 0 publications

Catechol Pyrazolinones as Trypanocidals: Fragment-Based Design, Synthesis, and Pharmacological Evaluation of Nanomolar Inhibitors of Trypanosomal Phosphodiesterase B1

Catechol Pyrazolinones as Trypanocidals: Fragment-Based Design, Synthesis, and Pharmacological Evaluation of Nanomolar Inhibitors of Trypanosomal Phosphodiesterase B1

Nematic Liquid Crystals: Physical Properties, Section 2.3

Diamagnetic Properties of Nematic Liquid Crystals

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