Synthesis of novel non-cross-linking pyrrolobenzodiazepines with remarkable DNA binding affinity and potent antitumour activity

Kamal, Ähmed; Laxman, N.; Ramesh, G.; Khairatkar-Joshi, Neelima; Kondapi, Anand K.

doi:10.1039/b009195m

Cited by 37 publications

(41 citation statements)

References 13 publications

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“…These activities, which result in their pharmacological utility, have been reported to be enhanced when different functionalities or substitutions are present on the two heterocyclic moieties in the bis-compound [24][25][26][27][28][29][30][31][32][33][34][35][36][37].…”

Section: Introductionmentioning

confidence: 99%

Efficient Routes for the Synthesis of Novel Bis(s‐triazolo[3,4‐b][1,3,4]thiadiazines)

Sarhan

Badawy

Elwahy

2014

Journal of Heterocyclic Chem

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Bis(triazolo[3,4‐b]thiadiazine) 4 in which the fused system is linked directly to the benzene core can be synthesized in 75% yield by, firstly, preparation of bis(s‐triazole) 2 followed by reaction with phenacyl bromide 3 in refluxing EtOH/DMF mixture containing piperidine. Bis(s‐triazolo[3,4‐b][1,3,4]thiadiazines) 8 and 11 in which the triazolothiadiazines are linked to benzene core via alkyl or ether linkage were synthesized in 70 and 72% yields, respectively, starting from dicarboxylic acids 5 and 9 upon treatment with two moles of thiocarbohydrazide 6 to give the corresponding bis(4‐amino‐5‐mercapto‐s‐triazolo‐3‐y1) derivatives 7 and 10 and subsequent reaction with two equivalents of phenacyl bromide. Bis(6‐phenyl‐7H‐[1,2,4]triazolo[3,4‐b][1,3,4]thiadiazines) 15a, 15b, 15c, 15d, 15e, 15f, which are linked to arene cores via sulfanylmethylene spacers, were prepared by the reaction of 4‐amino‐4H‐1,2,4‐triazole‐3,5‐dithiol 12 with the appropriate bis(bromomethyl)benzenes 13a, 13b, 13c, 13d, 13e, 13f to give bis(4‐amino‐5‐mercapto‐4H‐3‐sulfanylmethyl)arenes 14a, 14b, 14c, 14d, 14e, 14f and subsequent reaction with phenacyl bromide. Compounds 15a, 15b, 15c, 15d, 15e, 15f were alternatively obtained in 60–70% yields by twofold substitution of 13a, 13b, 13c, 13d, 13e, 13f with two equivalents of 6‐phenyl‐7H‐[1,2,4]triazolo[3,4‐b][1,3,4]thiadiazine‐3‐thiol 16 in refluxing EtOH/DMF mixture containing KOH. Bis(triazolothiadiazine) 22 attached to the benzene core through the thiadiazine ring via an amine linkage was prepared in 70% yield starting from p‐phenylenediamine 19 by, firstly, acylation with chloroacetyl chloride 18 followed by bis‐alkylation with 1,2,4‐triazole 20 and subsequent intramolecular ring closure upon treatment with phosphorus oxychloride.

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Section: Introductionmentioning

confidence: 99%

Efficient Routes for the Synthesis of Novel Bis(s‐triazolo[3,4‐b][1,3,4]thiadiazines)

Sarhan

Badawy

Elwahy

2014

Journal of Heterocyclic Chem

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“…Free amine 7 was generated in 83% yield from 6 using TMSI. Compound 7 was treated with the 4-bezyloxy-5-methoxy-2-nitro benzoyl chloride, 17,18 which was obtained from the corresponding acid, to afford the key intermediate amide 8. Reduction of the nitro group in 8 with SnCl 2 AE2H 2 O in methanol under reflux condition gave 9.…”

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confidence: 99%

Synthesis of a novel tetrahydroisoquinolino[2,1-c][1,4]benzodiazepine ring system with DNA recognition potential

Kothakonda

Bose

2004

Bioorganic & Medicinal Chemistry Letters

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“…These activities, that result in their pharmacological utility, have been reported to be enhanced when different functionalities or substitutions are present on the two heterocyclic moieties in the bis-compound. 3,4 However, there have been very few reports of this type of unsymmetrical bis compounds containing indole as the basic heterocyclic moiety. Thus, in continuation to our interest on spiro [5][6][7] and bis-spiro indoles, 8 we now wish to report the synthesis of some novel unsymmetrical bis-spiroindoles via their corresponding bis-Schiff's bases.…”

Section: Introductionmentioning

confidence: 99%

A facile synthesis of novel unsymmetrical bis-spiro[indole-pyrazolinyl-thiazolidine]-2,4'-diones

Jain¹,

Sakhuja²,

Khanna³

et al. 2008

Arkivoc

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Synthesis of novel non-cross-linking pyrrolobenzodiazepines with remarkable DNA binding affinity and potent antitumour activity

Cited by 37 publications

References 13 publications

Efficient Routes for the Synthesis of Novel Bis(s‐triazolo[3,4‐b][1,3,4]thiadiazines)

Efficient Routes for the Synthesis of Novel Bis(s‐triazolo[3,4‐b][1,3,4]thiadiazines)

Synthesis of a novel tetrahydroisoquinolino[2,1-c][1,4]benzodiazepine ring system with DNA recognition potential

A facile synthesis of novel unsymmetrical bis-spiro[indole-pyrazolinyl-thiazolidine]-2,4'-diones

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