1. Efficient synthesis of 2-aminoindane-2-carboxylic acid via dialkylation of nucleophilic glycine equivalent
Trevor K Ellis, Veronica M Hochla, Vadim A Soloshonok J Org Chem. 2003 Jun 13;68(12):4973-6. doi: 10.1021/jo030065v.
An efficient, easy to scale-up method for preparing 2-aminoindane-2-carboxylic acid via two-step alkylation of a Ni(II)-complex of glycine Schiff base with 2-[N-(alpha-picolyl)amino]benzophenone (PAAP) (2b) with o-dibromoxylylene (3) is reported. The first step, monoalkylation of 2b with 3, conducted under phase-transfer conditions, gave the corresponding complex 6 in excellent chemical yield (97.2%). Without any purification the intermediate 6 was cyclized under homogeneous conditions (DMF, NaO-t-Bu) to give the product 7 in high chemical yield (93.1%). Decomposition of prepared 7 afforded the target amino acid 2-aminoindane-2-carboxylic acid (1) in 97.9% yield, along with recovery of ligand 8, which was converted back to the starting glycine complex 2b. Operationally convenient experimental procedures, mild reaction conditions, as well as high chemical and volume yields render the method practical for preparing amino acid 1 and its analogues.
2. Design, Synthesis and Late-Stage Modification of Indane-Based Peptides via [2+2+2] Cyclotrimerization
Sambasivarao Kotha, Naveen Kumar Gupta, Gaddamedi Sreevani, Nageswara Rao Panguluri Chem Asian J. 2021 Nov 15;16(22):3649-3657. doi: 10.1002/asia.202100825. Epub 2021 Sep 22.
Here, we prepared several dipeptides containing 2-aminoindane-2-carboxylic acid (Aic) and carried out further synthetic transformations. Synthesis and purification of modified peptides by using [2+2+2] cyclotrimerization is a challenging task. We are able to modify the unusual amino acids and peptide derivatives by late-stage incorporation of benzylhalo functionality. To incorporate benzylhalo moiety we used [2+2+2] cyclotrimerization in the presence of Mo(CO)6 . These halo derivatives are potential substrates for further modification by Sonogashira reaction, Suzuki-Miyaura cross-coupling, sultine formation, and the Diels-Alder reaction sequence.
3. The effects of N-terminal part modification of arginine vasopressin analogues with 2-aminoindane-2-carboxylic acid: a highly potent V2 agonist
Wioleta Kowalczyk, Dariusz Sobolewski, Adam Prahl, Izabela Derdowska, Lenka Borovicková, Jirina Slaninová, Bernard Lammek J Med Chem. 2007 Jun 14;50(12):2926-9. doi: 10.1021/jm070174s. Epub 2007 May 15.
In this study we present the synthesis and some pharmacological properties of nine new analogues of arginine vasopressin modified in the N-terminal part of the molecule with 2-aminoindane-2-carboxylic acid (Aic). The peptides were tested for their in vitro uterotonic and in vivo pressor and antidiuretic activities. One of the new peptides, [Mpa1,Aic2,Val4,D-Arg8]VP, exhibited an antidiuretic activity similar to that of [Mpa1,D-Arg8]VP, thus being one of the most potent antidiuretic vasopressin analogues reported to date.
