Comparison of structure in solid state of new 1,5-bis(4-cyano-2,6-dimethoxyphenoxy)alkanes by means of 13C CP/MAS NMR and X-ray diffraction

Żabiński, Jerzy; Wolska, Irena; Maciejewska, Dorota

doi:10.1016/j.molstruc.2006.09.006

Cited by 9 publications

(10 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Their transformation into bisamidines followed the procedure for the rest of the bisnitriles (Scheme 2). Syntheses of the bisamidines 4 – 6 , 14 and 16 and bisnitriles 1a , 4a – 6a , 8a – 9a, 14a , 16a have been published by us [19–23] together with their structural analysis, and synthesis of the bisnitrile 18a was given in paper [24]. …”

Section: Resultsmentioning

confidence: 99%

Analogs of pentamidine as potential anti-Pneumocystis chemotherapeutics

Maciejewska

Żabiński

Kaźmierczak

et al. 2012

European Journal of Medicinal Chemistry

Self Cite

View full text Add to dashboard Cite

A series of 20 pentamidine analogs were prepared using 2 general Schemes that evaluated heteroatoms, sulfobenzene and alkanediamide groups in the aliphatic linker and methoxy substituents attached to the benzene rings for efficacy against the fungal pathogen, Pneumocystis carinii in an ATP bioassay. All but one of the 20 bisamidines reduced the ATP content of the P. carinii over the 72 hr of the assay period. The highest activities were associated with the lack of methoxy groups and the presence of the O, N and S heteroatoms. Activity (IC50) for compounds 1, 5, 6, 10 ranged from 1.1 to 2.13 µM. The compound 11 with similar activity (1.33 µM), bears a sulfobenzene group at a nitrogen in the aliphatic linker. The alkanediamide-linked bisbenzamidines showed a moderate inhibition of ATP. Generally, the inclusion of a heteroatom in the aliphatic linker and absence of methoxy groups at the benzene rings were associated with higher activities in this assay. Of note, most of the compounds had little to no cytotoxicity in mammalian cell cultures. Although not quite as potent as other pentamidine derivatives, these compounds hold promise for decreased side effects within the mammalian host.

show abstract

Section: Resultsmentioning

confidence: 99%

Analogs of pentamidine as potential anti-Pneumocystis chemotherapeutics

Maciejewska

Żabiński

Kaźmierczak

et al. 2012

European Journal of Medicinal Chemistry

Self Cite

View full text Add to dashboard Cite

show abstract

“…The non-hydrogen atoms in the molecule of the title compound are coplanar, with atoms N1, C7 and C8 deviating by 0.025 (2), 0.066 (2) and 0.042 (2) Å, respectively. The C≡N distance (1.1373 (17) Å) shows normal value (1.136 (2) Å; Zabinski et al, 2007).…”

Section: S1 Commentmentioning

confidence: 98%

“…For general background, see: Chihiro et al (1995); Diana et al (1993). For a related structure, see: Zabinski et al (2007).…”

Section: Related Literaturementioning

confidence: 99%

See 1 more Smart Citation

4-Hydroxy-3,5-dimethoxybenzonitrile at 125 K

Cheng

2007

Acta Cryst E

View full text Add to dashboard Cite

Key indicators: single-crystal X-ray study; T = 123 K; mean (C-C) = 0.002 Å; R factor = 0.041; wR factor = 0.113; data-to-parameter ratio = 17.3.In the title compound, C 9 H 9 NO 3 , all non-H atoms are coplanar. An O-HÁ Á ÁO hydrogen bond is observed in the molecular structure and intermolecular O-HÁ Á ÁN hydrogen bonds link the molecules into a chain along the a axis. Related literatureFor synthesis, see: Van Es (1965). For general background, see: Chihiro et al. (1995); Diana et al. (1993). For a related structure, see: Zabinski et al. (2007). Experimental Crystal data C 9 H 9 NO 3 M r = 179.17 Orthorhombic, Pbca a = 8.9624 (12) Å b = 12.5413 (16) Å c = 15.881 (2) Å V = 1785.1 (4) Å 3 Z = 8 Mo K radiation = 0.10 mm À1 T = 123 (2) K 0.50 Â 0.50 Â 0.40 mm Data collection Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2002) T min = 0.848, T max = 0.874 (expected range = 0.932-0.960) 17694 measured reflections 2036 independent reflections 1469 reflections with I > 2(I) R int = 0.034

show abstract

“…For another method of preparation of the title compound, see: Ushijima et al (2012). For the crystal structures of aromatic nitriles, see: Buschmann et al (1995); Zabinski et al (2007); Zanotti et al (1980).…”

Section: Related Literaturementioning

confidence: 99%

2,5-Dimethoxybenzonitrile

Bugenhagen¹,

Jasem²,

Thiemann³

2013

Acta Cryst E

View full text Add to dashboard Cite

In the title molecule, C9H9NO2, the non-H atoms are essentially coplanar with a maximum deviation of 0.027 (2) Å for the C atom of one of the methyl groups. In the crystal, the molecules are arranged into centrosymmetric pairs via pairs of C—H⋯O and C—H⋯N interactions whereas π–π stacking interactions between the benzene rings [centroid–centroid distance 3.91001 (15) Å] organize them into polymeric strands propagating along the a-axis direction. There is a step of 0.644 (2) Å between the two planar parts of the centrosymmetric pair. In neighboring strands related by the n-glide operation, the aromatic rings are tilted by 29.08 (2)°.

show abstract

Comparison of structure in solid state of new 1,5-bis(4-cyano-2,6-dimethoxyphenoxy)alkanes by means of 13C CP/MAS NMR and X-ray diffraction

Cited by 9 publications

References 16 publications

Analogs of pentamidine as potential anti-Pneumocystis chemotherapeutics

Analogs of pentamidine as potential anti-Pneumocystis chemotherapeutics

4-Hydroxy-3,5-dimethoxybenzonitrile at 125 K

2,5-Dimethoxybenzonitrile

Contact Info

Product

Resources

About