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4-Des-oxy-4β-[(5-meth-oxy-1H-indol-3-yl)oxalylamino]podophyllotoxin methanol solvate.

ABSTRACT: The main mol-ecule of the title solvate, C(33)H(30)N(2)O(10)·CH(3)OH, is a new anti-tumor agent, which shows cytotoxicity against MDR cancer cell lines. It has been synthesized by coupling 4β-amino-podophyllotoxin with (5-meth-oxy-1H-indol-3-yl)glyoxyl chloride and structurally characterized. There are two crystallographically independent mol-ecules in the asymmetric unit, which differ in the dihedral angles between the aromatic rings. The dihedral angles between the benzene ring of the benzo[d][1,3]dioxole and the benzene ring of the 5-meth-oxy-1H-indole are 85.08 (3) and 76.88 (3)° and reflect the main conformational difference between the two independent mol-ecules. The asymmetric unit is completed with two methanol solvent mol-ecules, one of which is disordered over two positions, with occupancies close to 0.5.

SUBMITTER: Feng M

PROVIDER: S-EPMC2959988 | biostudies-literature |

REPOSITORIES: biostudies-literature

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5-Meth-oxy-1-[(5-meth-oxy-1H-indol-2-yl)meth-yl]-1H-indole.

Project description:In the title compound, C(19)H(18)N(2)O(2), the two indole ring systems are essentially planar [maximum deviation = 0.015 (2) Å in both indole ring systems] and make a dihedral angle of 72.17 (7)° with each other. In the crystal, the mol-ecules are linked into a zigzag chain along the a axis via N-H⋯O hydrogen bonds.

| S-EPMC3343946 | biostudies-literature

5-Meth-oxy-3-[(5-meth-oxy-1H-indol-3-yl)(phen-yl)meth-yl]-1H-indole.

Project description:In the title compound, C(25)H(22)N(2)O(2), the indole rings are individually almost planar [with maximum deviations of 0.0116 (19) and 0.0113 (18) Å] and are almost orthogonal to each other, making a dihedral angle of 84.49 (6)°. The benzene ring is inclined at 72.83 (9) and 80.85 (9)° with respect to the indole rings. In the crystal, mol-ecules are linked by N-H⋯O inter-actions into chains running parallel to the c axis. The crystal structure is further stabilized by C-H⋯π inter-actions.

| S-EPMC3238863 | biostudies-literature

5-Meth-oxy-2-[(5-meth-oxy-1H-indol-1-yl)carbon-yl]-1H-indole.

Project description:The asymmetric unit of the title compound, C(19)H(16)N(2)O(3), comprises three independent mol-ecules (A, B and C). The inversion-related molecule of A is virtually superimposable upon the other two molecules. In each mol-ecule, there is a twist in the link between the approximately syn carbonyl and amine groups [the N-C-C-O torsion angles range from 19.73?(19) to -21.2?(2)°]. Each mol-ecule has a bent shape quanti-fied in terms of the dihedral angle between the indole and indole fused-ring systems [range = 45.69?(5)-47.91?(5)°]. In the crystal, the A and B mol-ecules form dimeric aggregates via ten-membered {?HNC(2)O}(2) synthons, while the C mol-ecules self-associate similarly but about a centre of inversion.

| S-EPMC3379355 | biostudies-literature

(5-Meth-oxy-1H-indol-3-yl)acetonitrile.

Project description:In the title compound, C(11)H(10)N(2)O, the O atom and the C atom of the methyl-ene group deviate only slightly [0.029?(3) and 0.055?(3)?Å, respectively] from the approximately planar ring system (r.m.s. deviation = 0.013?Å). In the crystal, N-H?O hydrogen bonds link the mol-ecules into zigzag chains running along the b axis.

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2-(4-Meth-oxy-1H-indol-3-yl)acetonitrile.

Project description:In the title compound, C(11)H(10)N(2)O, the cyanide group is twisted away from the indole-ring plane [C(cy)-C(me)-C(ar)-C(ar) = 70.7 (2)°; cy = cyanide, me = methyl-ene, ar = aromatic], whereas the meth-oxy C atom is almost coplanar with the ring system [displacement = 0.014 (5) Å]. In the crystal, N-H⋯N hydrogen bonds link the mol-ecules into C(7) chains propagating in [100].

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Methyl [hydr-oxy(phen-yl)phosphono-meth-yl]phospho-nate methanol solvate.

Project description:The title compound, C(8)H(12)O(7)P(2)·CH(4)O, is a monoesterified bis-phospho-nate (or 1-hydroxy-methyl-ene-1,1-bis-phospho-nic acid). These synthetic compounds are widely used in medicine to inhibit bone resorption in diseases like osteoporosis, and are characterized by a stable P-C-P group and are thus analogs of inorganic pyrophosphate. By masking one or several ionizable groups, introduced as phosphono-ester, it was anti-cipated the formation of prodrugs with higher lipophilicity that could facilitate the drug delivery and metabolization. Mol-ecules are paired by inter-molecular hydrogen bonds involving the phospho-nic groups. In addition, dimers are connected side-by-side, building infinite ribbons along the a-axis direction; these ribbons are cross-linked perpendicularly along the b-axis direction via a methanol solvent mol-ecule (disordered over two sites with occupancy factors ca 0.6 and 0.4), forming an extended inter-molecular hydrogen-bonded network. The H atoms of the methyl group in the main molecule are disordered equally over two positions.

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Methyl 4-(5-meth-oxy-1H-indol-3-yl)benzoate.

Project description:In the title compound, C(17)H(15)NO(3), the dihedral angle between the benzene ring and the indole ring system is 22.5?(3)°. In the crystal, mol-ecules are linked by N-H?? and C-H?O inter-actions.

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2-(1-Ethyl-5-meth-oxy-1H-indol-3-yl)-N-(4-meth-oxy-phen-yl)-2-oxoacetamide.

Project description:The title compound, C(20)H(20)N(2)O(4), crystallizes with four independent mol-ecules in the asymmetric unit. In the mol-ecules, the dihedral angles between the benzene rings and indole mean planes are 24.5 (1), 22.5 (1), 8.8 (1) and 13.9 (1)°. In the crystal, inter-molecular N-H⋯O hydrogen bonds are present between the imino groups and the adjacent carbonyl groups. π-π stacking is also observed with a centroid-centroid distance between nearly parallel pyrrole rings of 3.745 (3) Å.

| S-EPMC3051647 | biostudies-literature

Ethyl 2-(5-meth-oxy-2-methyl-1H-indol-3-yl)acetate.

Project description:In the title compound, C14H17NO3, the nine-membered 1H-indole ring system is essentially planar [maximum deviation = 0.019 (1) Å]. In the crystal, mol-ecules are linked via N-H⋯O hydrogen bonds, forming chains along [001]. These chains are linked via C-H⋯O hydrogen bonds and C-H⋯π inter-actions, forming a two-dimensional network lying parallel to the ac plane.

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(5-Ethenyl-1-aza-bicyclo-[2.2.2]octan-2-yl)(6-meth-oxy-3-quinol-yl)methanol methanol solvate.

Project description:In the title methanol solvate, C(20)H(24)N(2)O(2)·CH(4)O, an L-shaped conformation is found as the two substituents at the central hydr-oxy group are almost orthogonal to each other [the C-C-C angle at the central sp(3)-C atom is 110.12?(13)°]. The most notable feature of the crystal packing is the formation of supra-molecular chains along the b direction mediated by O-H?N hydrogen bonds occurring between the hydr-oxy and quinoline N atoms; the methanol mol-ecules are linked to these chains via O-H?N(amine) hydrogen bonds. C-H?O inter-actions also occur.

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