Ancistrotanzanine C and Related 5,1‘- and 7,3‘-Coupled Naphthylisoquinoline Alkaloids fromAncistrocladustanzaniensis

Bringmann, Gerhard; Dreyer, Michael; Faber, Johan H.; Dalsgaard, Petur Weihe; Stærk, Dan; Jaroszewski, Jerzy W.; Ndangalasi, Henry J.; Mbago, Frank M.; Brun, Reto; Christensen, Søren Brøgger

doi:10.1021/np0340549

Cited by 166 publications

(98 citation statements)

References 28 publications

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“…Extended interest to the Schiff bases is caused by their use as starting materials in the synthesis of important drugs, such as antibiotics and antimalarial, antifungal, and antitumor substances [1][2][3][4][5], as components of rubber compounds [6], or as ligands for the complexation of metal ions [7][8][9]. The bond lengths and angles in the title crystal structure are in normal ranges.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of (E)-4-chloro-2-(isopropyliminomethyl)phenol, C10H12ClNO

Lin¹,

Zhou²,

Wu³

et al. 2010

Zeitschrift Für Kristallographie - New Crystal Structures

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C 10 H 12 ClNO, monoclinic, C12/c1(no. 15), a =21.459(2) Å, b =5.6893(6) Å, c =17.760(2) Å, b =105.137(2)°, Source of materialAll reagents and solvents were used as purchased without further purification. 5-chloro-2-hydroxybenzaldehyde (147 mg, 1m mol), propan-2-amine (118 mg, 2m mol) were dissolved in methanol (15 mL). The mixture was refluxd for aperiod of 8h and, after cooling to room temperature, was filtered. The filtrate was kept still in air for one week. Large block-shaped crystals were precipitated. They were filtered and washed with ethanol and dried in avacuum desiccator using anhydrous CaCl 2 (yield 89 %). Experimental detailsAll Hatoms were positioned geometrically and refined as riding with d(C-H) =0.93 -0.98 Å), U iso (H) =1.2 or 1.5 U eq (C), respectively. The instability of isopropyl group and the poor quality of the crystals result in quite large residual values. DiscussionExtended interest to the Schiff bases is caused by their use as starting materials in the synthesis of important drugs, such as antibiotics and antimalarial, antifungal, and antitumor substances [1][2][3][4][5], as components of rubber compounds [6], or as ligands for the complexation of metal ions [7][8][9]. The bond lengths and angles in the title crystal structure are in normal ranges. The C7=N1 bond length of 1.263(4) Å conforms to the value of adouble bond. The torsion angle N1-C7-C1-C6 is -178.94(3)°.Inthe crystal packing, the molecules are linked by several weak intermolecular C-H···Ointeractions.

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Section: Discussionmentioning

confidence: 99%

Crystal structure of (E)-4-chloro-2-(isopropyliminomethyl)phenol, C10H12ClNO

Lin¹,

Zhou²,

Wu³

et al. 2010

Zeitschrift Für Kristallographie - New Crystal Structures

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“…[5][6] . They are also used as intermediates in organic synthesis as well as polymers stabilizers 7 .…”

Section: Research Articlementioning

confidence: 99%

Preparation, Spectroscopy and X-Ray Structure Analysis of N, Nʹ-Bis(3-nitrophenylmethylene)- cyclohexane-1,2-diamine

2017

Chem Sci Trans

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The compound N,cyclohexane-1,2-diamine (α-diimine Shiff base) was synthesized and characterized by MS, IR, NMR 1 H and X-ray single crystal analysis. While the cyclohexane-1,2-diamine used for the synthesis of this composite is a racemic cis and trans mixture, we observed by x-ray diffraction for the product N,N'-bis(3-nitrophenylmethylene) cyclohexane-1,2-diamine only the (1R,2R)trans enantiopure. The crystalline network cohesion of this compound is assured by a combination of C-H ... O and C-H ... N hydrogen bonds. It crystallizes in the monoclinic non-standard I2/a space group.

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“…Imine or azomethine groups are present in various natural, naturally-derived, and nonnatural compounds. The imine group present in such compounds has been shown to be critical to their biological activities [3][4][5]. For this reason, Schiff bases, which are very easy to synthesize, constitute an inexhaustible source of promising versatile pharmacophores for the design and development of new biologically important molecules.…”

Section: Introductionmentioning

confidence: 99%