182823-26-3Relevant articles and documents
Microwave assisted synthesis of pyrrolo[2,1-c][1,4]benzodiazepine-5,11- diones
Kamal, Ahmed,Reddy, B.S. Narayan,Reddy, G. Suresh Kumar
, p. 1251 - 1252 (1999)
In a simple microwave assisted and environmentally benign approach isatoic anhydride reacts readily with proline to afford pyrrolo[2, 1- c][1,4]benzodiazepines-5,11-diones under solvent-free conditions.
Influence of temperature for the azide displacement in benzodiazepine derivatives: Experimental and DFT study of competing SN1, SN2 and double SN2 reaction pathways
Evangelista, Tereza Cristina Santos,Delarmelina, Maicon,Addla, Dinesh,All?o, Rafael A.,Kaiser, Carlos Roland,Carneiro, José Walkimar de M.,Silva-Jr, Floriano Paes,Ferreira, Sabrina Baptista
, (2021)
Molecules carrying the azido functionality are widely used as intermediates in medicinal chemistry. Pyrrolobenzodiazepines are molecules with a broad range of interesting pharmacological properties. Due to the wide importance of azido-PBD as a key interme
Synthesis of a novel C2-aryl pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione library: Effect of C2-aryl substitution on cytotoxicity and non-covalent DNA binding
Antonow, Dyeison,Jenkins, Terence C.,Howard, Philip W.,Thurston, David E.
, p. 3041 - 3053 (2007)
A 23-member C2-aryl pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione (PBD dilactam) library has been synthesized using Suzuki coupling, and the effect of base upon racemisation at the C11a-position during the cross-coupling reaction studied. Three library members (21, 30 and 33) were sufficiently cytotoxic in the NCI's preliminary screen to warrant further evaluation, and one (30, R = p-Br) was found to be cytotoxic at the sub-micromolar level in the A498 renal cancer cell line. DNA thermal denaturation studies suggested that this activity may be associated with non-covalent DNA interaction, and also demonstrated that introductin of C2-C3 unsaturation and addition of C2-aryl functionalities to the PBD dilactam skeleton significantly enhanced helix stabilisation compared to the unsubstituted PBD dilactam (6).
One-Step Preparation of Pyrrolo[1,4]benzodiazepine Dilactams: Total Synthesis of Oxoprothracarcin, Boseongazepines B and C
Smits, Gints,Zemribo, Ronalds
, p. 2272 - 2276 (2015/09/28)
A one-step synthesis of pyrrolo[1,4]benzodiazepine dilactams has been developed. The high yielding method involves direct coupling of unprotected anthranilic acids with proline esters. This transformation was successfully applied in the first total syntheses of boseongazepines B and C as well as oxoprothracarcin and limazepine E.
Design, synthesis and evaluation of novel 2-hydroxypyrrolobenzodiazepine-5, 11-dione analogues as potent angiotensin converting enzyme (ACE) inhibitors
Addla, Dinesh,Jallapally, Anvesh,Kanwal, Abhinav,Sridhar, Balasubramanian,Banerjee, Sanjay K.,Kantevari, Srinivas
, p. 4485 - 4493 (2013/07/26)
A series of novel 10-substituted 2-hydroxypyrrolobenzodiazepine-5,11-diones designed through structure based rational hybridization approach, synthesized by the cyclodehydration of isotonic anhydride with (2S,4R)-4-hydroxypyrrolidine- 2-carboxylic acid followed by N-substitution, were evaluated as angiotensin converting enzyme (ACE) inhibitors. Among all the new compounds screened (2R,11aS)-10-((4-bromothiophen-2-yl)methyl)-2-hydroxy-2,3-dihydro-1H-benzo[e] pyrrolo[1,2-a][1,4]diazepine-5,11(10H,11aH)dione, 5v (IC50: 0.272 μM) emerged as most active non-carboxylic acid ACE inhibitor with minimal toxicity comparable to clinical drugs Lisinopril, Benazepril and Ramipril. Favorable binding characteristics in docking studies also supported the experimental results.
One-pot microwave-assisted selective azido reduction/tandem cyclization in condensed and solid phase with nickel boride
Shankaraiah, Nagula,Markandeya, Nagula,Espinoza-Moraga, Marlene,Arancibia, Claudia,Kamal, Ahmed,Santos, Leonardo Silva
experimental part, p. 2163 - 2170 (2009/12/31)
An efficient and inexpensive method using microwave-assisted irradiation with Ni2B for the syntheses of aromatic amines, pyrrolobenzodiazepines as well as pyrroloquinazolinones was developed. This protocol was applied in the tandem resin-cleavage, azido reduction, and cyclization of compounds 3 and 5 that afforded substituted pyrrolo[2,1-c][1,4] benzodiazepines 4 and 6 in a one-pot manner. The microwave-assisted irradiation reactions enhanced yields with very short reaction times in contrast to the conventional thermal reactions. Georg Thieme Verlag Stuttgart.
Chemoselective aromatic azido reduction with concomitant aliphatic azide employing Al/Gd Triflates/Nal and ESI-MS mechanistic studies
Kamal, Ahmed,Markandeya, Nagula,Shankaraiah, Nagula,Ratna Reddy,Prabhakar,Sanjeeva Reddy,Eberlin, Marcos N.,Santos, Leonardo Silva
experimental part, p. 7215 - 7224 (2010/03/05)
Aluminium and gadolinium inflates catalyze the chemoselective reduction of aromatic azides to the corresponding amines in combination with sodium iodide. This mild chemoselective method has been applied to the synthesis of various aryl amines, C2azido-substituted pyrrolo[2,1-c]-[1,4]benzodiazepines, and fused[2,1b]quinazolinones by an intramolecular azido reduction tandem cyclization reaction. Interestingly, this methodology selectively reduces aryl azides with enhanced yields and proceeds in shorter reaction times than previous strategies. The mechanistic aspects have been investigated and the intermediates associated with this selective transformation have been intercepted and characterized by online monitoring of the reaction by ESI-MS.
Design, synthesis, and in vitro activity of peptidomimetic inhibitors of myeloid differentiation factor 88
Fantò, Nicola,Gallo, Grazia,Ciacci, Andrea,Semproni, Mauro,Vignola, Davide,Quaglia, Marco,Bombardi, Valentina,Mastroianni, Domenico,Zibella, M. Pia,Basile, Giancarlo,Sassano, Marica,Ruggiero, Vito,De Santis, Rita,Carminati, Paolo
, p. 1189 - 1202 (2008/09/20)
We describe the design and synthesis of a peptidomimetic library derived from the heptapeptide AC-RDVLPGT-NH2, belonging to the Toll/IL-1 receptor (TIR) domain of the adaptor protein MyD88 and effective in inhibiting its homodimerization. The a
An efficient selective reduction of aromatic azides to amines employing BF3·OEt2/NaI: Synthesis of pyrrolobenzodiazepines
Kamal, Ahmed,Shankaraiah,Markandeya,Reddy, Ch. Sanjeeva
experimental part, p. 1297 - 1300 (2009/04/06)
A selective and facile method for the reduction of aromatic azides to amines by employing borontrifluoride diethyl etherate and sodium iodide. This methodology has been applied towards the preparation of biologically important imine-containing pyrrolobenzodiazepines and their dilactams through intramolecular reductive-cyclization process. In this protocol the reagent systems are amenable for the generation of solution-phase combinatorial synthesis. Georg Thieme Verlag Stuttgart.
Selective reduction of aromatic azides in solution/solid-phase and resin cleavage by employing BF3·OEt2/EtSH. Preparation of DC-81
Kamal, Ahmed,Shankaraiah,Reddy, K. Laxma,Devaiah
, p. 4253 - 4257 (2007/10/03)
An efficient method for the reduction of aromatic azides in both solution and solid-phase has been developed by employing BF3·OEt2/EtSH. This report also describes resin cleavage employing this reagent system. Further, this protocol has been utilized for the solution as well as the solid-phase synthesis of pyrrolo[2,1-c][1,4]benzodiazepines, including the naturally occurring antibiotic DC-81 and fused [2,1-b]quinazolinones.
