4-Desoxy-4β-[(5-methoxy-1H-indol-3-yl)oxalylamino]podophyllotoxin methanol solvate

Abstract

The main mol­ecule of the title solvate, C33H30N2O10·CH3OH, is a new anti­tumor agent, which shows cytotoxicity against MDR cancer cell lines. It has been synthesized by coupling 4β-amino­podophyllotoxin with (5-meth­oxy-1H-indol-3-yl)glyoxyl chloride and structurally characterized. There are two crystallographically independent mol­ecules 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-meth­oxy-1H-indole are 85.08 (3) and 76.88 (3)° and reflect the main conformational difference between the two independent mol­ecules. The asymmetric unit is completed with two methanol solvent mol­ecules, one of which is disordered over two positions, with occupancies close to 0.5.

2-(1-Ethyl-5-methoxy-1H-indol-3-yl)-N-isopropyl-2-oxoacetamide

“…In title compound, C 16 H 20 N 2 O 3 , bond lengths and angles are normal and in good agreement with those reported previously (Feng et al, 2008;Sonar, et al, 2006). π-π interactions are indicated by the short distance (Cg1•••Cg2 distance of 3.693 (9) Å, Cg2•••Cg2 distance of 3.577 (9)Å symmetry code: 1 -x,1 -y,-z) between the centroids of the pyrrole ring (N1/C1/C6-C8) (Cg1) and benzene ring C1-C6 (Cg2) (…”

N-Cyclohexyl-2-(5-methoxy-1H-indol-3-yl)-2-oxoacetamide

“…In (I) ( Fig. 1), all bond lengths and angles are normal and in a good agreement with those reported previously (Feng et al, 2008;Sonar et al, 2006). The cyclohexane ring (C12-C17) adopts a chair conformation.…”

“…For details of the synthesis, see: Bacher et al (2001). For similar structures, see: Feng et al (2008); Sonar et al (2006).…”

9-[(Furan-2-ylmethyl)amino]-5-(3,4,5-trimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3′,4′:6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one

“…In title compound, bond lengths and angles are normal and in good agreement with those reported previously for related compounds (Feng et al, 2008;Zhang, et al, 1994;Zuo, et al, 2009). The tetrahydrofuran ring (C15-C18/O4) and the six-membered ring (C6-C7/C13-C15/C18) fused to it both display envelope conformations.…”

“…The furan ring is disordered over two sets of sites with occupancies of 0.722 (7) and 0.278 (7) Related literature For podophyllotoxin derivatives synthesized by our group, see: Lu et al (2010); Yu et al (2008); Zhao et al (2009). For bond-length and angle data of related structures, see: Feng et al (2008); Zhang et al (1994); Zuo et al (2009 Table 1 Hydrogen-bond geometry (Å , ). Symmetry codes: (i) Àx þ 2; y þ 1 2 ; Àz þ 1; (ii) Àx þ 1; y þ 1 2 ; Àz þ 1; (iii) x À 1; y; z; (iv) Àx þ 1; y À 1 2 ; Àz þ 2.…”