ChemInform Abstract: A Novel, Broad‐Spectrum Anticancer Compound Containing the Imidazo[4,5‐e][1,3]diazepine Ring System.
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Abstract Synthesis and broad‐spectrum anticancer activity of novel compounds containing the title diazepine ring system are reported.Keywords:
Diazepine
Broad spectrum
Abstract The thieno[3,2‐ e ][1,4]diazepin‐2‐one ( 1a ), the thieno[2,3‐ e ] [ 1,4] diazepin‐2‐one ( 1b ), the pyrazolo[3,4‐ e ][1,4]diazepin‐2‐one ( 1c ) and a chloro analog of 1b , compound 1 d , were each converted to derivatives of the novel tricyclic ring systems 4 H ‐imidazo[1,5‐ a ]thieno[2,3‐ f ] [1,4]‐diazepine, 4 H imidazo[1,5 a ]thieno[2,3 f ][1,4]diazepine and 4 H ‐imidazo[ 1,5‐a]pyrazolo[4,3‐ f ]‐[1,4]diazepine. Depending on the substituents desired on the imidazo ring, two different synthetic pathways were employed.
Diazepine
Tricyclic
D-1
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Abstract Five variants (methods A—E) of a synthetic route to 6‐amino‐1‐benzyl‐4‐methylhexahydro‐1 H ‐1,4‐diazepine (3b) using N ‐benzyl‐ N' ‐methylethylenediamine (8a) are described. The reaction of 8a with 1‐benzenesulfonyl‐2‐bromomethylaziridine (7) , 2‐phenyl‐4‐( p ‐toluenesulfonyloxymethyl)oxazoline (13) , and β, β‐dibromoisobutyric acid (15) resulted in the direct cyclization to give the precursor of 3b , 6‐substituted 1,4‐diazepine derivatives 9, 14 , and 16 , respectively (methods A—C). These compounds were transformed into the desired 3b , The preparation of 1,4‐diazepine ring from methyl 2‐ tert ‐butoxycarbonyl‐aminopropenate (18) was alternatively achieved by the intramolecular amidation of the intermediate 19a (method D) or reductive cyclization of the aminoaldehyde 23a (method E). Method E was found to efficiently produce the 6‐amino‐1,4‐diazepine 3b.
Diazepine
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The title compound, C(26)H(22)N(2)O(2), features a benzene ring fused with a seven-membered diazepine ring; the latter ring adopts a boat conformation (with the propargylallyl-bearing C atom as the prow and the fused-ring C atoms as the stern). The phenyl ring of one of the two benzyl substituents is disordered over two positions in a 0.812 (11):0.188 (11) ratio.
Diazepine
Propargyl
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The title compound, C(26)H(24)N(2)O(2), features a benzene ring fused with a seven-membered diazepine ring; the latter ring adopts a boat conformation (with the allyl-dimethyl-amino-methyl-bearing C atom as the prow and the fused-ring C atoms as the stern).
Diazepine
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The title compound, C(25)H(23)N(3)O, features a benzene ring fused with a seven-membered 1,4-diazepine ring; the latter ring adopts a boat conformation with the (dimethyl-amino)methyl-bearing C atom as the prow and the fused-ring C atoms as the stern. There are two independent mol-ecules in the asymmetric unit with similar conformations.
Diazepine
Methylene
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In the title compound, C14H19ClN2O, the diazepine ring adopts a boat conformation. The Cl atom of the chloro-acetyl group is trans to the N atom of the diazepine ring. In the crystal, the mol-ecules form chains running along the diagonal of the ac plane through N-H⋯O hydrogen bonds.
Diazepine
Crystal (programming language)
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Abstract Syntheses of 4, 5, 6, 8-tetrahydro-1H, 7H-imidazo[4, 5-d] [1, 3]-diazepine-5, 8-dione (9), its 3-benzyl derivative (8), and 3- and 1-ribosyl derivatives, (12) and (13), respectively, are reported. Single-crystal x-ray analyses of 8 and 9 are also presented.
Diazepine
Derivative (finance)
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The title compound, C43H32N2O3, has a cis ring-fusion tricyclic structure, which is formed from a benzene ring, a seven-membered diazepine ring and a 1,3-oxazinone ring. The 1,5-diazepine ring has a slightly distorted boat-like conformation, whereas the 1,3-oxazinone ring adopts a half-chair conformation.
Diazepine
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Synthesis of a series of novel, broad-spectrum anti-cancer agents containing the tricyclic 5:7:5-fused diimidazo[4,5-d:4',5'-f][1,3]diazepine ring system is reported. Compounds 1, 2, 8, 11, and 12 in the series show promising in vitro antitumor activity with low micromolar IC(50)'s against prostate, lung, breast, and ovarian cancer cell lines. Some notions about structure-activity relationships and a possible mechanism of biological activity are presented. Also presented are preliminary in vivo toxicity studies of 1 using SCID mice.
Tricyclic
Broad spectrum
Diazepine
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