Deuterium Exchange of the α-Methylene Group Protons in the Quinazolones. III. Environment Influence on the Exchange Rate

By 1H NMR spectroscopy methods the exchange process of α-methylene group protons of deoxyvasicinone by deuterium atoms in the medium of CD3OD+NaOH and CD3OD+CD3COOD depending on NaOH concentration and temperature of the solution and CD3COOD have been investigated. It was shown that NaOH and CD3COOD have exchange initiator character, and their effect on the concentration are linear to D-exchange rate. The exponential dependence on temperature allowed us to determine the potential barrier of the initiation of the D- exchange process for deoxyvasicinone in the CD3COOD

(E)-3-Propoxymethyl­idene-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one monohydrate

The title compound, C15H16N2O2·H2O, was synthesized via the alkyl­ation of 3-hydroxy­methyl­idene-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one with n-propyl iodide in the presence of sodium hydroxide. The organic mol­ecule and the water mol­ecule both lie on a crystallographic mirror plane. In the crystal structure, inter­molecular O—H⋯O and O—H⋯N hydrogen bonds link the components into extended chains along [100]

2,3-Dihydro­pyrrolo­[2,1-b]quinazoline-9(1H)-thione

In the crystal, mol­ecules of the title compound, C11H10N2S, are connected by C—H⋯N inter­actions around threefold axes. Furthermore, they form stacks along the c axis showing π–π inter­actions between pyrimidine rings [centroid–centroid distance = 3.721 (1) Å]. The central ring is essentially planar with an r.m.s. deviation of 0.007 Å. The five-membered ring adopts an envelope conformation with the flap atom deviating by 0.241 (4) Å from the mean plane (r.m.s. deviation = 0.002 Å) through the other four ring atoms

2-Methyl-4-oxo-6,7,8,9-tetrahydro­thieno[2′,3′:4,5]pyrimidino­[1,2-a]pyridine-3-carboxylic acid

There are two independent mol­ecules in the asymmetric unit of the title compound, C12H12N2O3S. With the exception of the methyl­ene groups, a mean plane fitted through all non-H atoms of each mol­ecule has an r.m.s. deviation of 0.035 Å for one mol­ecule and 0.120 Å for the second. In one of the independent mol­ecules, the methyl­ene groups was refined using a disorder model with an occupancy ratio of 0.53:0.47 (14). Each molecule features an intra­molecular O—H⋯O hydrogen bond, which generates an S(7) ring

(E)-3-[4-(Dimethyl­amino)­benzyl­idene]-2,3-di­hydro-1H,9H-pyrrolo­[2,1-b]quinazolin-9-one

The title compound, C20H19N3O, was obtained by condensation of 2,3-dihydro-1H,9H-pyrrolo­[2,1-b]quinazolin-9-one (alkaloid de­oxy­vasicinone, isolated from Peganum Harmala) with 4-(dimethyl­amino)­benzaldehyde in the presence of sodium methoxide. The 2,3-dihydro-1H,9H-pyrrolo­[2,1-b]quinazolin-9-one part of the mol­ecule is roughly planar (r.m.s. deviation = 0.0178 Å) and is essentially coplanar with the benzil­idene ring (r.m.s. deviation = 0.0080 Å), forming a dihedral angle of 5.0 (1)°. The crystal structure is stabilized by two aromatic π–π stacking inter­actions observed between the benzene rings of neighboring mol­ecules [centroid–centroid distance = 3.7555 (19) Å

Synthesis of Substituted Thieno[2,3- d

From 2-amino-3-ethoxycarbonyl-4,5-dimethyl-, -polymethylenethiophenes (1-4) were synthesized 2,3-disubstituted thieno[2,3-d]dihydropyrrolo-, tetrahydropyrido-, and tetrahydroazepino[1,2-a]pyrimidin-4-ones (5-16) for pharmacological investigations. The 12 compounds (5-16) were individually evaluated for their antiproliferative activities on mammalian cancer cell models. All tested compounds showed weak affection on human cervix adenocarcinoma cells (HeLa) whereas some of the tested compounds exhibited more consistent inhibition of cell growth on murine myeloma cells (P3X). In both cases some compounds enhanced cell proliferation

(4-Nitrophenyl)(1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-3-yl)methanol monohydrate

In the crystal structure of the title compound, C18H17N3O3·H2O, the molecules are linked by O—H...O and O—H...N hydrogen bonds, resulting in a chain along the a axis. The crystal structure is stabilized by weak intermolecular C—H...π (ring) hydrogen bonds and aromatic π...π stacking interactions [centroid–centroid distance = 3.902 (1) Å] between the pyrimidino rings of the quinazoline system. The tricyclic quinazoline fragment is almost planar (rms deviation = 0.0139 Å) with the two methylene C atoms of the pyrrolo ring deviating by 0.148 (2) and −0.081 (3) Å from the plane through the other atoms. The 4-nitrophenyl ring makes a dihedral angle of 12.55 (7)° with the tricyclic ring system