, C5), 117.five (C), 119.0 (C), 120.four (CH), 120.four (CH), 120.6 (CH), 121.1 (CH), 122.4 (CH), 127.five (C, Cb), 128.eight (CH
, C5), 117.five (C), 119.0 (C), 120.4 (CH), 120.4 (CH), 120.six (CH), 121.1 (CH), 122.4 (CH), 127.five (C, Cb), 128.8 (CH), 128.9 (CH), 137.0 (C), 138.3 (CH, C4″), 144.three (CH, C6), 145.9 (C, Ca), 148.2 (CH, C6″), 150.2 (C, C2″). Crystal data for 5i. C20 H14 N4 , M = 310.35, T = 150(2) K, triclinic, P-1, a = 7.0573(ten), b = eight.3875(11), c = 13.563(two) = 87.146(5), = 75.381(five), = 72.673(five) , V = 741.31(19) , Z = two, d = 1.390 g cm-3 , = 0.086 mm-1 . A final refinement on F2 with 3361 unique intensities and 217 parameters GNE-371 supplier converged at R(F2 ) = 0.0994 (R(F) = 0.0389) for 2635 observed reflections with I 2(I). CCDC 2109702. three.7.4. 2-(1-Indolyl)-1-(5-(1-indolyl)-2-thienyl)-7-azaindole (6g ) The basic process 9 (reaction time: 24 h) from 2-iodo-1-(5-iodo-2-thienyl)-1Hpyrrolo[2,3-b]pyridine (3g ; 0.23 g) afforded (eluent: petroleum ether-EtOAc 80:20) the title product in 20 yield as a yellow oil. IR: 422, 659, 714, 737, 761, 801, 881, 902, 929, 965, 1012, 1043, 1071, 1106, 1127, 1207, 1266, 1303, 1316, 1336, 1347, 1387, 1412, 1450, 1474, 1504, 1517, 1568, 1594, 1713, 2923, 2960, 3050. 1 H-NMR (CDCl3 ): six.61 (dd, 1H, J = three.3 and 0.9 Hz), six.69 (dd, 1H, J = three.3 and 0.9 Hz), 6.77 (s, 1H), six.77 (d, 1H, J = 3.six Hz), six.80 (d, 1H, J = 4.0 Hz), 7.15.28 (m, 6H), 7.29 (dd, 1H, J = 7.9 and four.9 Hz), 7.39 (t, 1H, J = eight.2 Hz), 7.62 (dd, 1H, J = six.5 and 1.two Hz), 7.68 (dd, 1H, J = six.4 and two.0 Hz), 8.04 (dd, 1H, J = 7.9 and 1.six Hz), 8.51 (dd, 1H, J = 4.eight and 1.6 Hz). 13 C-NMR (CDCl3 ): 98.7 (CH), 104.five (CH), 105.2 (CH), 110.7 (CH), 110.7 (CH), 118.4 (CH), 118.9 (CH), 120.0 (C), 121.1 (CH), 121.1 (CH), 121.two (CH), 121.three (CH), 123.0 (CH), 123.2 (CH), 123.four (CH), 128.7 (C), 128.8 (CH), 129.1 (CH), 129.1 (C), 129.three (CH), 130.7 (C), 135.2 (C), 137.0 (C), 138.0 (C), 139.eight (C), 144.8 (CH, C6), 147.six (C, Ca). Anal. Calc. for C27 H18 N4 S (430.53): C 75.33, H 4.21, N 13.01. Identified: C 75.11, H four.46, N 12.65. three.eight. Evaluation from the Biological Properties The antibacterial, antifungal and antioxidant activity was determined as described previously [77]. 4. Conclusions Our objective within the present paper was to rationalize the conversion of 1-aryl-7-azaindoles into either the corresponding 2-iodo derivatives (by deprotometalation-iodolysis) or the corresponding 3-iodo derivatives (by direct iodination). This could possibly be accomplished by calculat-Molecules 2021, 26,29 ofing either the pKa values or the HOMO orbital coefficients, respectively. The atomic charges also allowed the regioselectivity of these reactions to become predicted. As a result, the obtained iodides have been converted into derivatives with promising biological properties.Supplementary Materials: The following data are obtainable on-line. The NMR information of the compounds 2k, 2k , 3a, 3a , 3e , 3g , 3k, 3k , 3k”, 4b , 4h, 4i, 5e, 5i and 6g ; the ML-SA1 web calculated values of your Gibbs energies Gacid [kJ ol-1 ] for deprotonation, the cartesian coordinates of molecular geometry for essentially the most stable rotamer form optimized in the B3LYP/6-31G(d) level of theory in the .xyz format. Author Contributions: M.Y.A.M. synthesized all compounds presented within this write-up and analyzed most of them; G.B.-A. supervised; M.H. and Z.F. performed the bioassays. Y.S.H., O.A.I. and V.E.M. performed the computations. T.R. and V.D. collected all X-ray diffraction data and solved the structures. F.M. wrote the paper together with the assistance of Z.F., Y.S.H., T.R. and V.D. All authors have read and agreed towards the published version of your manuscript. Funding: This study received no external f.