362612-68-8

Provided herein are pyrrolopyrimidine compounds of Formula (I) wherein R1 is a heteroaryl containing at least one S atom, and optionally substituted on a ring carbon by one, two, or three substituents each independently selected from the group consisting of : halo, hydroxyl, nitro, formyl, formamido, cyano, sulfonyl, carboxy, amino, amido, acylamino, carbamoyl, sulphamoyl, alkyl, alkenyl, CF3, ureido, alkynyl, alkoxy, alkanoyl, alkoxycarbonyl, carbaldehyde oxime, N -alkylsulphamoyl, N-alkylcarbamoyl, -OR13R11 or -R13R11; R2 is phenyl or pyridinyl, wherein R2 optionally substituted on a ring carbon by one, two, or three substituents each indenpendently selected from the group consisting of : halo, hydroxyl, cyano, nitro, formyl, formamido, carboxy, sulfonyl, amino, amido, -N- alkyl -amino, carbamoyl, sulphamoyl, CF3, ureido, alkyl, alkenyl, alkynyl, alkoxy, alkanoyl, alkoxycarbonyl, N-alkylsulphamoyl, N-alkylcarbamoyl, -OR11, -OR12R11, or -R12R11; and methods of making and using the same. Such compounds may be used in inflammatory or myeloproliferative disorders. The disclosure also provides for treating cancer.

The ramifications of changing molecular geometry in a series of all-aromatic liquid crystals derived from p-quinquephenyl are reported. Substituting heterocyclic rings such as thiophene, oxadiazole, oxazole, or 1,3-phenylene into the p-quinquephenylene core affects molecular shape changes via the substituent's exocyclic bond angle. In general, we found that introducing nonlinearity into molecules depresses the melting transition temperature. The symmetric (boomerang-shaped) molecules, 2,5-bisbiphenyl-4-yl-1,3,4-oxadiazole, 2,5-bisbiphenyl-4-yl-oxazole, and 1,3-bisbiphenyl-4-yl-benzene, melt into isotropic phases showing small monotropic mesophases. By contrast, the asymmetric (hockey stick-shaped) mesogens, 2-terphenyl-4-yl-5-phenyl thiophene and 2-terphenyl-4-yl-5-phenyl-1,3,4-oxadiazole, exhibit more stable enantiotropic liquid crystalline phases. The hockey stick-shaped mesogens exhibit a smectic phase as well as a nematic phase. High-temperature X-ray determination of the smectic layer spacing gives an unambiguous picture of interdigitated, bilayerlike supramolecular architecture in the smectic phase. There are associated changes in the mesogen's electrostatic profile when a heterocycle is introduced into the quinquiphenylene framework (e.g., conjugation is perturbed). Our findings suggest that steric packing considerations dominate the phase preferences (nematic versus smectic phases). However, electronic considerations (conjugation) appear to control the range of mesomorphism in this new family of nonlinear liquid crystals.