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4-Chloro-7-methoxy-methyl-2-phenyl-7H-pyrrolo[2,3-b]pyridine.

ABSTRACT: In the title compound, C(15)H(13)ClN(2)O, the phenyl group makes a dihedral angle of 7.91 (8)° with the pyrrole ring. The crystal structure forms a three-dimensional network stabilized by π-π inter-actions [centroid-centroid distances = 3.807 (1) Å] between the pyridine and phenyl rings and via inter-molecular C-H⋯O hydrogen bonds.

SUBMITTER: Selig R

PROVIDER: S-EPMC2983947 | biostudies-literature |

REPOSITORIES: biostudies-literature

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4-Chloro-1-(4-methyl-phenyl-sulfon-yl)-1H-pyrrolo[2,3-b]pyridine.

Project description:The crystal structure of the title compound, C(14)H(11)ClN(2)O(2)S, features a three-dimensional network stabilized by ?-? inter-actions between the rings of the 4-methyl-phenyl-sulfonyl protecting group [centroid-centroid distance = 3.623?(1)?Å]. The 4-methyl-phenyl-sulfonyl ring makes a dihedral angle of 79.60?(6)° with the 4-chloro-1H-pyrrolo[2,3-b]pyridine unit.

| S-EPMC2972132 | biostudies-literature

7-(4-Methoxy-phen-yl)-5-methyl-9-phenyl-7H-pyrrolo[2',3':4,5]pyrimido[1,6-d]tetrazole.

Project description:The title compound, C(20)H(16)N(6)O, is composed of a tetra-zolo ring and a 4-methoxy-phenyl and a benzene-substituted pyrrole ring at the 7 and 9 positions fused to a pyrimidine ring in a nearly planar fashion [maximum deviation of 0.018?(1)?Å for the fused ring system]. A methyl group at the 5 position is also in the plane of the hetero cyclic system. The dihedral angle between the mean planes of the benzene and 4-methoxy-phenyl rings is 40.4?(2)°. The dihedral angles between the mean planes of the pyrimidine and the benzene and 4-methoxy-phenyl rings are 15.6?(5)° and 52.6?(7)°, respectively. A weak intra-molecular C-H?N hydrogen bond inter-action, which forms an S(7) graph-set motif, helps to establish the relative conformations of the tetrazolo and benzene rings. In the crystal, weak inter-molecular C-H?O, C-H?? and ?-? stacking inter-actions [centroid-centroid distances = 3.5270?(16), 3.5113?(16), 3.7275?(17) and 3.7866?(17)?Å] link the mol-ecules into a two-dimensional array obliquely parallel to (101) and propagating along the b axis.

| S-EPMC2980237 | biostudies-literature

5-Chloro-N-[2-(1H-imidazol-4-yl)eth-yl]-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine.

Project description:The title compound, C(12)H(13)ClN(6), was prepared by reaction of 4,5-dichloro-7H-pyrrolo[2,3-d]pyrimidine with 2-(1H-imid-azol-4-yl)-N-methyl-ethanamine, and the X-ray study confirmed that chloro-substituent in six-membered ring was replaced in the reaction. The exocyclic N atom environment is approximately coplanar with the pyrrolo[2,3-d]pyrimidine [corresponding dihedral angle is 5.5?(1)°], whereas the mean plane of the N-C-C-C link connecting with the imidazolyl ring is almost exactly orthogonal to the plane of the bicyclic system [dihedral angle = 91.6?(2)°]. The imidazolyl plane itself, however, forms a relatively small dihedral angle of 20.8?(1)° with the pyrrolo[2,3-d]pyrimidine plane. There are two independent N-H?N hydrogen bonds in the structure, which link mol-ecules into layers parallel to (03).

| S-EPMC2980157 | biostudies-literature

5-(4-Chloro-phen-yl)-7-(4-methyl-phen-yl)-4-(pyrrolidin-1-yl)-7H-pyrrolo-[2,3-d]pyrimidine.

Project description:The title compound, C23H21ClN4, contains two molecules (A and B) in the asymmetric unit, which are related to one another by a pseudo-inversion center. The non-aromatic pyrrolidine ring in each independent mol-ecule adopts a half-chair conformation; the ring puckering parameters are θ = 0.407 (3) Å and ϕ = 270.5 (4)°, and the pseudo-rotation parameters are ρ = 72.5 (3)° and τ = 42.2 (2)° for an N-C bond of molecule A, and the corresponding values are 0.415 (3) Å, 271.6 (4)°, 73.6 (3)° and 42.6 (2)° for molecule B. The dihedral angles between the central fused-ring system and the substituted chlorophenyl and methylphenyl rings are 66.35 and 45.59°, respectively, for molecule A, and 64.51 and 41.89° for molecule B. The geometry of all four intramolecular C-H⋯π interactions are of type III. π-π interactions involving the centroids of symmetry-related pyrrole rings of molecule B are 4.390 Å, contributing further to the stability of the molecule.

| S-EPMC3793780 | biostudies-literature

1-Methyl-7-(4-nitro-phen-yl)-3-phenyl-pyrazolo[3,4-b]pyrrolo[3,4-d]pyridine-6,8(3H,7H)-dione.

Project description:In the title compound, C(21)H(13)N(5)O(4), the dihedral angles formed between the planes of the phenyl and nitro-phenyl rings and that of the heterotricyclic plane are 41.29 (7) and 61.35 (6)°, respectively. In the crystal, weak C-H⋯O interactions help to establish the packing.

| S-EPMC2959918 | biostudies-literature

7-(4-Chloro-phen-yl)-9-phenyl-7H-pyrrolo[3,2-e]tetra-zolo[1,5-c]pyrimidine.

Project description:In the title compound, C(18)H(11)ClN(6), the pyrrole, pyrimidine and tetra-zole rings form a nearly planar fused trihetrocyclic system with an r.m.s. deviation of 0.0387?(13)?Å, to which the 4-chloro-phenyl group and the phenyl group are substituted at the 7 and 9 positions, respectively. The dihedral angles between the pyrrole ring and the 4-chloro-phenyl and phenyl rings are 32.1?(4) and 7.87?(7)°, respectively. In the crystal, weak inter-molecular C-H?N and C-H?Cl hydrogen bonds link the mol-ecules into a layer parallel to the (001) plane. The layers are further connected by ?-? stacking inter-actions [centroid-centroid distances: 3.8413?(8) and 3.5352?(8)?Å]. Intra-molecular C-H?N hydrogen bonds are also present.

| S-EPMC2983688 | biostudies-literature

Synthesis of 5,7-disubstituted-4-methyl-7H-pyrrolo[2,3-d]pyrimidin-2-amines as microtubule inhibitors.

Project description:Compounds 1-4 were previously reported as potent antimitotic and antitumor agents with Pgp modulatory effects. Compounds 5-18 have been synthesized in an attempt to optimize the various activities of 1-4. Compounds 5-10 explored the influence of methoxy substitutions on the 7-benzyl moiety in 1, while 11-18 investigated the influence of incorporation of a sulfur linker at C5 compared to 1-3. Compounds 5-10 demonstrated potent single-digit micromolar tumor cell cytotoxicity, Pgp modulation and microtubule inhibition. Compound 7 of this series was the most potent and showed GI(50) values in the nanomolar range against several human tumor cell lines in the standard NCI preclinical in vitro screen. Antitumor activity and Pgp modulatory effects were found to decrease for the 5-phenylthio compounds 11-14 compared to their 5-phenylethyl analogs 2-4 and the standard compound Taxol. Incorporation of methoxy substitutions on the 7-benzyl moiety improved antitumor activity for the 5-phenylthio compounds 16 and 17. Compounds 16 and 17 demonstrated single to two-digit micromolar inhibition of tumor cells.

| S-EPMC3582361 | biostudies-literature

N-[(3RS,4RS)-1-Benzyl-4-methyl-piperidin-3-yl]-5-nitro-1-phenyl-sulfonyl-1H-pyrrolo-[2,3-b]pyridine-4-amine.

Project description:The pyrrolo-pyridine system in the title compound, C(27)H(29)N(5)O(4)S, is oriented at a dihedral angle of 71.20?(5)° towards the phenyl ring of the tosyl residue and at a dihedral angle of 45.43?(4)° towards the benzyl group. The structure shows an intra-molecular N-H?O and a weak intra-molecular N-H?N hydrogen bond. The piperidine ring adopts a chair conformation, with the cis substituents displaying a torsion angle of -54.59?(18)°.

| S-EPMC3470400 | biostudies-literature

5-Bromo-1H-pyrrolo-[2,3-b]pyridine.

Project description:In the title compound, C7H5BrN2, fused six-membered pyridine and five-membered pyrrole rings form the essentially planar aza-indole skeleton (r.m.s. deviation = 0.017?Å). In the crystal, pairs of N-H?N hydrogen bonds connect the mol-ecules into inversion dimers.

| S-EPMC3588463 | biostudies-literature

7-Phenyl-sulfonyl-7H-benzofurano[2,3-b]carbazole.

Project description:In the title compound, C(24)H(15)NO(3)S, the dihedral angle between the phenyl ring and the carbozole system is 74.91 (6)°. The S atom exhibits a distorted tetra-hedral geometry [N-S-C = 104.85 (8)°; O-S-O = 119.59 (9)°]. The crystal structure is established by weak inter-molecular π-π inter-actions [centroid-centroid distances = 3.583 (2)-3.782 (2) Å].

| S-EPMC3247568 | biostudies-literature

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