Bile Acid Amphiphiles with Tunable Head Groups as Highly Selective Antitubercular Agents
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1 Electronic Supplementary Material (ESI) for Medicinal Chemistry Communications. This journal is The Royal Society of Chemistry 204 Supporting Information Bile Acid Amphiphiles with Tunable Head Groups as Highly Selective Antitubercular Agents Sandhya Bansal, a, Manish Singh, a, Saqib Kidwai, b, Priyanshu Bhargava, a Ashima Singh, a Vedagopuram Sreekanth, a Ramandeep Singh, b, * and Avinash Bajaj a, * a The Laboratory of Nanotechnology and Chemical Biology, Regional Centre for Biotechnology, 80 Udyog Vihar, Phase, Gurgaon-2206, Haryana, India. b Vaccine and Infectious Disease Research Centre, Translational Health Science and Technology Institute, 496 Udyog Vihar Phase III, Gurgaon- 2206, Haryana, India. These Authors contributed equally. *Corresponding Author: Ramandeep Singh: ramandeep@thsti.res.in, Avinash Bajaj: bajaj@rcb.res.in, Ph: , Fax:
2 Table S: Topological parameters of E. coli and M. bovis BCG probed by AFM showing the selective membrane perturbations of E. coli by CA-AMM 3 and of M. bovis BCG by CA- DMAP 3. E. coli Length (μm) Width (μm) Height (nm) Corrugation (nm) Control 2.57 ± ± ± ± 0.79 CA-AMM ± ± ± ± 4.40 CA-DMAP ± ± ± ±.62 M. bovis (BCG) Length (μm) Width (μm) Height (nm) Corrugation (nm) Control 4.4 ± ± ± ±.57 CA-AMM ± ± ± ±.28 CA-DMAP ± ± ± ±
3 Fig. S. Cytotoxic activities of bile acid facial amphiphiles at different concentrations against lung epithelial A549 cells. 3
4 Fig. S2. Cytotoxic activities of bile acid facial amphiphiles at different concentrations against macrophage THP- cells. 4
5 Fig. S3: Cell cycle analysis of cholic acid based amphiphiles against A549 cells showing no change in cell cycle phase of cells up at 00 M concentration of hard-charged amphiphiles. 5
6 % Hemolysis µm 500 µm 000 µm % Hemolysis µm 500 µm 000 µm 0 LCA-AMM LCA-TMA LCA-PIP LCA-PYR LCA-DMAP 0 CDCA-AMM 2 CDCA-TMA 2 CDCA-PIP 2 CDCA-PYR 2 CDCA-DMAP 2 % Hemolysis µm 500 µm 000 µm % Hemolysis µm 500 µm 000 µm 0 DCA-AMM 2 DCA-TMA 2 DCA-PIP 2 DCA-PYR 2 DCA-DMAP 2 0 CA-AMM 3 CA-TMA 3 CA-PIP 3 CA-PYR 3 CA-DMAP 3 Fig. S4: Hemolytic activities of bile acid amphiphiles showing percentage of hemolysis at 250, 500 and 000 M concentrations of bile acid amphiphiles. 6
7 Fig. S5. Concentration and time dependent activities of CA-AMM 3 (a, c) and CA-DMAP 3 (b, d) against E. coli (a, b) and S. aureus (c, d) bacteria showing their selective killing by soft-charged amphiphile CA-AMM 3. 7
8 Synthesis of bile acid facial amphiphiles: Synthesis of Bile Acid Amphiphiles Chloroacteryl derivatives of bile acid methyl esters (3a-3d) was synthesized as described earlier (Biochim. Biophys. Acta Biomembr. 203, 828, 926). Bile Acid amphiphiles were synthesized by quaterinization of corresponding chloroacteryl derivatives of bile acid methyl esters in ethyl acetate (5 ml) in seal tube with corresponding amine derivative. The reaction mixture was heated at 70 o C for 48h-72h. After completion of reaction, solvent was removed and repeated washing with ethyl acetate or acetone give purified product. LCA-AMM : H NMR (CDCl 3, 400 MHz) δ: 0.64 (s, 3H, -CH 3 ), 0.9 (s, 6H, -2 x CH 3 ), (steroid), 3.66 (s, 3H, -CO-OCH 3 ), 3.90 (m, 2H, -CO-CH 2 -N-), 4.82 (s, H, -O-CH), 8.49 (bs, 2H, - NH 2 ). 3 C-NMR (DMSO, 00 MHz) δ: 2.30, 8.56, 20.84, 23.22, 24.27, 26.40, 26.54, 27.00, 28.5, 30.82, 3.06, 32.3, 34.59, 34.74, 35.25, 35.73, 4.47, 42.72, 5.69, 55.9, 56.37, 76.09, 67.58, HRMS (ESI-MS): m/z (C 27 H 46 NO 4 ) + calculated ; found (M) LCA-TMA : H-NMR (CDCl 3, 400 MHz) δ: 0.63 (s, 3H, -CH 3 ), 0.9 (s, 6H, -2 x CH 3 ), (steroid), 3.64(s, 9H, -N-(CH 3 ) 3 ; 3H, -CO-OCH 3 ), 4.78 (m, H, -O-CH), 4.84 (m, 2H, -CO-CH 2 -N- ). 3 C-NMR (CDCl 3, 00 MHz) δ: 2.05, 8.28, 20.25, 23.22, 24.7, 26.2, 26.40, 26.94, 28.8, 3.0, 8
9 3.08, 3.98, 34.55, 34.86, 35.37, 35.76, 39.98, 40.37, 4.94, 42.73, 5.5, 54.28, 55.89, 56.28, 63.34, 77.24, 77.96, 64.24, HRMS (ESI-MS): m/z (C 30 H 52 NO 4 ) + calculated (M) ; found (M) LCA-PIP : H-NMR (CDCl 3, 400 MHz) δ: 0.6 (s, 3H, -CH 3 ), 0.88 (s, 3H, -CH 3 ), 0.90 (s, 3H, -CH 3 ), (steroid), 3.59 (s, 3H, -N-CH 3 ), 3.63 (s, 3H, -CO-OCH 3 ), 3.9 (m, 2H, -N-CH 2 ), 4.2 (m, 2H, -N-CH 2 ), 4.9 (m, 3H, -O-CH, -CO-CH 2 -N-). 3 C-NMR (CDCl 3, 00 MHz) δ: 2.04, 8.27, 20.25, 20.83, 23.22, 24.6, 26.22, 26.4, 26.93, 28.7, 3.00, 3.07, 3.98, 34.55, 34.86, 35.36, 35.76, 40.00, 40.39, 4.92, 42.72, 47.89, 5.49, 55.9, 56.33, 6.06, 6.42, 77.25, 77.73, 64.27, HRMS (ESI-MS): m/z (C 33 H 56 NO 4 ) + calculated ; found (M) LCA-PYR : H-NMR (CDCl 3, 400 MHz) δ: 0.62 (s, 3H, -CH 3 ), 0.90 (s, 6H, -2 x CH 3 ), (steroid), 3.65 (s, 3H, -CO-OCH 3 ), 4.78 (m, H, -O-CH), 6.26 (s, 2H, -CO-CH 2 -N-), 8.05 (s, 2H, ArH), (m, H, ArH), 9.40 (s, 2H, ArH). 3 C-NMR (CDCl 3, 00 MHz) δ: 2.05, 8.28, 20.86, 23.24, 24.8, 26.25, 26.48, 26.95, 28.8, 3.08, 32.0, 34.55, 34.88, 35.38, 35.77, 40.0, 40.39, 4.94, 42.73, 5.50, 55.9, 56.34, 6.27, 78.53, 27.55, 39.52, 45.94, 65.55, HRMS (ESI-MS): m/z (C 32 H 48 NO 4 ) + calculated (M) ; found (M) LCA-DMAP : H-NMR (CDCl 3, 400 MHz) δ: 0.63 (s, 3H, -CH 3 ), 0.89 (s, 3H, -CH 3 ), 0.90 (s, 3H, - CH 3 ) (steroid), 3.26 (s, 6H, -N(CH 3 ) 2 ), 3.65 (s, 3H, -CO-OCH 3 ), 4.76 (m, H, -O-CH), 4.84 (m, 2H, -CO-CH 2 -N-), 6.89 (d, J = 7.2 Hz, 2H, ArH), 8.48 (d, J = 6.8 Hz, 2H, ArH). 3 C-NMR (CDCl 3, 00 MHz) δ: 2.04, 8.27, 20.84, 23.25, 24.7, 26.24, 26.48, 26.97, 28.6, 3.0, 3.07, 32.05, 34.55, 34.92, 35.35, 35.78, 40.02, 40.38, 40.42, 4.95, 42.73, 5.47, 55.90, 56.32, 57.82, 77.23, 77.70, 07.57, 43.98, 56.54, 66.74, HRMS (ESI-MS) : m/z (C 34 H 53 N 2 O 4 ) + calculated (M) ; found (M)
10 CDCA-AMM 2 : H-NMR (CDCl 3, 400 MHz) δ: 0.64 (s, 3H, -CH 3 ), 0.92 (s, 6H, -2 x CH 3 ), (steroid), 3.65 (s, 3H, -CO-OCH 3 ), (m, 4H, (-CO-CH 2 -N-) 2 ), 4.62 (s, H, -O-CH), 4.90 (s, H, -O-CH). 3 C-NMR (DMSO, 00 MHz) δ:.96, 8.55, 20.65, 22.93, 23.70, 26.76, 28.03, 30.76, 3.0, 3.28, 34.00, 34.56, 34.78, 35.7, 37.53, 4.5, 4.67, 42.73, 50.7, 5.69, 55.63, 72.74, 75.23, 69.53, 69.9, HRMS (ESI-MS): m/z (C 29 H 49 N 2 O 6 ) + calculated ; found (M) CDCA-TMA 2 : H-NMR (CDCl 3, 400 MHz) δ: 0.64 (s, 3H, -CH 3 ), 0.92 (d, J=6.4, 3H, -CH 3 ), 0.93 (s, 3H, -CH 3 ), (steroid), 3.60(m, 9H, -N-(CH 3 ) 3, 3.63(s, 3H, -CO-OCH 3 ), 3.65(s, 9H, -N-(CH 3 ) 3, 4.68 (m, 2H, -CO-CH 2 -N-), 4.80 (m, H, -CO-CH 2 -N-; H, -O-CH), 5.04 (s, H, -O-CH), 5.46 (m, H, -CO-CH 2 -N-), 5.66 (m, H, -CO-CH 2 -N-). -). 3 C-NMR (CDCl 3, 00 MHz) δ:.70, 8.23, 20.57, 22.53, 23.75, 26.37, 28.07, 29.70, 3.02, 3.08, 3.3, 34.00, 34.64, 34.73, 35.35, 37.92, 39.2, 40.58, 42.79, 50.07, 5.49, 53.99, 54.0, 55.4, 62.74, 63.0, 74.43, 75.38, 77,23, 64.64, 64.82, HRMS (ESI-MS): m/z (C 35 H 62 N 2 O 6 ) +2 calculated ; found (M) +2 / , M +2 Cl - calculated ; found M 2+ Cl CDCA-PIP 2 : H-NMR (CDCl 3, 400 MHz) δ: 0.63 (s, 3H, -CH 3 ), 0.9 (s, 6H, 2 x -CH 3 ), (steroid), 3.55 (s, 6H, -N-(CH 3 ) 2 ), 3.63 (s, 3H, -CO-OCH 3 ), (m, 8H, 2 -CH 2 -N-CH 2 -), 4.55 (m, H, -CO-CH 2 -N-), 4.82 (m, H, -CO-CH 2 -N-; H, -O-CH), -), 5.02 (s, H, -O-CH), -), 5.59 (m, 2H, -CO-CH 2 -N-). 3 C-NMR (DMSO, 00 MHz) δ:.7, 8.2, 20.6, 20.24, 20.56, 20.84, 20.89, 22.47, 23.79, 26.35, 28.07, 29.69, 30.97, 3., 3.22, 34., 34.59, 34.63, 34.7, 35.37, 37.86, 39.25, 42.8, 46.55, 50.26, 5.48, 55.47, 80.52, 6.0, 6.56, 6.90, 62.4, 65.84, 74.39, 75.08, 64.48, 64.73, HRMS (ESI-MS): m/z (C 4 H 70 N 2 O 6 ) 2+ calculated ; found (M) 2+ / , M 2+ Cl - calculated ; found M 2+ Cl CDCA-PYR 2 : H NMR (MeOH, 400 MHz) δ: 0.72 (s, 3H, -CH 3 ), 0.98 (s, 6H, -2 x CH 3 ), (steroid), 3.68 (s, 3H, -CO-OCH 3 ), 4.82 (m, H, -O-CH), 5. (s, H, -O-CH), (m, 4H, -CO- 0
11 CH 2 -N-, -CO-CH 2 -N-), 8.2 (t, 2H, J = 6.8Hz, ArH), 8.28 (t, 2H, J = 6.8Hz, ArH), 9.9 (m, H, ArH). 3 C-NMR (DMSO, 00 MHz) δ: 0.65, 7.30, 20.24, 2.5, 23.4, 26.33, 27.64, 30.4, 30.74, 30.80, 34.04, 34.29, 34.4, 34.50, 35.25, 37.75, 39.39, 40.67, 42.59, 50.3, 50.63, 55.79, 60.70, 75.2, 77.8, 27.70, 28.0, 46.28, 46.6, 46.80, 64.89, 65.64, HRMS (ESI-MS): m/z (C 39 H 54 N 2 O 6 ) 2+ calculated ; found (M) 2+ / , M 2+ Cl - calculated ; found M 2+ Cl CDCA-DMAP 2 : H NMR (CDCl 3, 400 MHz) δ: 0.6 (s, 3H, -CH 3 ), 0.98 (s, 6H, -2 x CH 3 ), (steroid), 3.24 (s, 6H, -N(CH 3 ) 2 ), 3.30 (s, 6H, -N(CH 3 ) 2 ), 3.65 (s, 3H, -CO-OCH 3 ), 4.72 (m, H, -O- CH), 4.93 (m, H, -O-CH), (m, 2H, -CO-CH 2 -N-), (m, 2H, -CO-CH 2 -N-), 6.93 (d, J = 6.4 Hz, 2H, ArH), 7.00 (d, J = 6.4 Hz, 2H, ArH), 8.56 (d, J = 6Hz, 2H, ArH), 8.79 (s, 2H, ArH). 3 C-NMR (DMSO, 00 MHz) δ:.65, 8.32, 20.53, 22.50, 23.60, 28.02, 29.70, 3.00, 3.09, 34.08, 34.6, 34.7, 35.29, 37.85, 39.44, 40.44, 40.55, 40.67, 42.77, 50.2, 5.57, 55.94, , , 77.26, 07.55, 07.73, 43.98, 44.26, 56.50, 56.52, 66.49, 67.22, HRMS (ESI- MS): m/z (C 43 H 64 N 4 O 6 ) 2+ calculated ; found (M) 2+ / , M 2+ Cl - calculated ; found M 2+ Cl DCA-AMM 2 : H-NMR (CDCl 3, 400 MHz) δ: 0.73 (s, 3H, -CH 3 ), 0.83 (s, 3H, -CH 3 ), 0.99 (s, 3H, - CH 3 ), (steroid), 3.64 (s, 3H, -CO-OCH 3 ), (m, 4H, (-CO-CH 2 -N-) 2 ), 4.74 (s, H, -O- CH), 5.6 (s, H, -O-CH). 3 C-NMR (DMSO, 00 MHz) δ:.27, 6.64, 20.65, 2.99, 23.05, 25.37, 25.69, 26.22, 26.58, 27.00, 30.40, 30.52, 3.76, 33.82, 34.28, 34.35, 34.72, 35.56, 40.30, 4.78, 44.96, 49.40, 50.63, 76.34, 78.02, 67.6, 68.00, 74.99, HRMS (ESI-MS): m/z (C 29 H 49 N 2 O 6 ) + calculated ; found (M) DCA-TMA 2 : H-NMR (CDCl 3, 400 MHz) δ: 0.75 (s, 3H, -CH 3 ), 0.84 (d, J = 2, 3H, -CH 3 ), 0.92 (s, 3H, -CH 3 ), (steroid), 3.55 (m, 9H, -N-(CH 3 ) 3, 3.60 (s, 4H, -N-(CH 3 ) 3, 3.66 (s, 3H, -CO- OCH 3 ), 3.68 (s, 5H, -N-(CH 3 ) 3, 4.63 (d, J = 7.6 Hz, H, -CO-CH 2 -N-), 4.80 (m, H, -O-CH), 5.6 (d,
12 J=6.8, H, -CO-CH 2 -N-), 5.28 (s, H, -O-CH), 5.53 (d, J = 7.2 Hz, H, -CO-CH 2 -N-), 5.62 (d, J = 7.2 Hz, H, -CO-CH 2 -N-). 3 C-NMR (CDCl 3, 00 MHz) δ: 2.27, 7.68, 22.53, 23.35, 25.84, 26.46, 27.32, 30.5, 3.03, 33.8, 33.95, 34.38, 34.64, 35.3, 4.32, 45.3, 49.30, 5.57, 54.04, 55.98, 63.2, 77.23, 78.99, 64.64, 64.82, HRMS (ESI-MS): m/z (C 35 H 62 N 2 O 6 ) 2+ calculated ; found (M) 2+ / , M 2+ Cl - calculated ; found M 2+ Cl DCA-PIP 2 : H-NMR (CDCl 3, 400 MHz) δ: 0.78 (s, 3H, -CH 3 ), 0.83 (d, J = 6.4, 3H, -CH 3 ), 0.97 (s, 3H, -CH 3 ), (steroid), 3.50 (s, 3H, -N-CH 3 ), 3.62 (s, 3H, -N-CH 3 ), 3.64 (s, 3H, -CO-OCH 3 ), (m, 8H, 2 -CH 2 -N-CH 2 -), 4.58 (m, H, -CO-CH 2 -N-), 4.78 (s, H, -O-CH), 5.09 (m, H, -CO- CH 2 -N-, 5.23 (s, H, -O-CH), -), 5.27 (m, 2H, -CO-CH 2 -N-), 5.42 (m, 2H, -CO-CH 2 -N-), 3 C-NMR (CDCl 3, 00 MHz) δ: 2.27, 7.73, 20.5, 20.36, 20.80, 20.85, 22.50, 23.37, 25.25, 25.82, 25.99, 26.44, 27.39, 30.57, 3.04, 3.0, 33.79, 34.44, 34.73, 35.32, 4.30, 45., 49.9, 5.60, 60.38, 6.04, 6.43, 62.68, 75.88, 77.24, 79.02, 64.32, 64.80, HRMS (ESI-MS): m/z (C 4 H 70 N 2 O 6 ) 2+ calculated ; found (M) 2+ / , M 2+ Cl - calculated ; found M 2+ Cl DCA-PYR 2 : H-NMR (CDCl 3, 400 MHz) δ: 0.7 (s, 3H, -CH 3 ), 0.85 (d, J = 6.4, 3H, -CH 3 ), 0.88 (s, 3H, -CH 3 ), (steroid), 3.67 (s, 3H, -CO-OCH 3 ), 4.82 (m, H, -O-CH), 5.29 (m, H, -O-CH), 6.25 (d, J = 7.2 Hz, 2H, -CO-CH 2 -N-), 6.44 (d, J =5.6 Hz, 2H, -CO-CH 2 -N-), 8.05 (t, 2H, J = 6.8 Hz, ArH), 8.26 (t, J = 6.8 Hz, 2H, ArH), 8.48 (t, J = 7.2 Hz, H, ArH), 8.70 (t, J = 7.2 Hz, 2H, ArH), 9.58 (m, 4H, ArH). 3 C-NMR (MeOH, 00 MHz) δ:.24, 6.76, 2.92, 23.07, 25.36, 25.80, 26.32, 26.57, 27.02, 30.45, 30.58, 3.76, 33.87, 34.23, 34.39, 34.83, 35.46, 4.72, 45.2, 47.0, 48.2, 49., 50.7, 60.72, 77.56, 79., 28.75, 28.2, 46.26, 46.63, 46.96, 64.58, 65.7, HRMS (ESI-MS): m/z (C 39 H 54 N 2 O 6 ) 2+ calculated ; found (M) 2+ / , M 2+ Cl - calculated ; found M 2+ Cl
13 DCA-DMAP 2 : H NMR (CDCl 3, 400 MHz) δ: 0.70 (s, 3H, -CH 3 ), 0.82 (s, 3H, -CH 3 ), 0.86 (s, 3H, - CH 3 ), (steroid), 3.23 (s, 6H, -N(CH 3 ) 2 ), 3.33 (s, 6H, -N(CH 3 ) 2 ), 3.66 (s, 3H, -CO-OCH 3 ), 4.78 (s, H, -O-CH), 5.20 (s, H, -O-CH), (m, 2H, -CO-CH 2 -N-), (m, 2H, -CO-CH 2 -N- ), 6.85 (s, 2H, ArH), 7.07 (s, 2H, ArH), 8.56 (s, 2H, ArH), 8.83 (s, 2H, ArH). 3 C-NMR (CDCl 3, 00 MHz) δ: 2.24, 7.77, 22.48, 23.35, 25.27, 25.96, 26.26, 26.45, 27.37, 30.7, 3.6, 3.30, 33.72, 33.85, 24.5, 34.77, 35.24, 40.32, 40.83, 4.34, 45.6, 47.24, 49.46, 5.59, 57.66, 57.82, 76.49, 77.35, 78.60, 07.37, 07.89, 43.93, 44.42, 56.49, 56.57, 65.94, 67.35, HRMS (ESI-MS): m/z (C 43 H 64 N 4 O 6 ) +2 calculated ; found (M) +2 / , M +2 Cl - calculated ; found M 2+ Cl CA-AMM 3 : H-NMR (CDCl 3, 400 MHz) δ: 0.74 (s, 6H, -2CH 3 ), 0.94 (d, J = 2.8 Hz, 3H, -CH 3 ), (steroid), 3.65 (s, 3H, -CO-OCH 3 ), (m, 4H, (-CO-CH 2 -N-) 2 ), 4.70 (s, H, -O-CH), 5.6 (s, H, -O-CH), 5.24 (s, H, -O-CH). 3 C-NMR (DMSO, 00 MHz) δ: 2.26, 7.63, 2.58, 22.53, 22.66, 22.72, 22.96, 25.65, 30.78, 34.42, 34.48, 34.68, 37.34, 39.4, 39.62, 39.83, 40.03, 40.24, 40.45, 40.66, 4.68, 43.09, 45.8, 45.2, 47.6, 5.65, 72.22, 75.34, 76.35, 69.77, 70.00, 7.90, HRMS (ESI-MS): m/z (C 3 H 52 N 3 O 8 ) + calculated ; found (M) CA-TMA 3 : H-NMR (CDCl 3, 400 MHz) δ: 0.74 (s, 3H, -CH 3 ), 0.84 (s, 3H, -CH 3 ), 0.94 (s, 3H, -CH 3 ), (steroid), 3.52 (s, 9H, -N-(CH 3 ) 3, 3.6 (s, 2H, -N-(CH 3 ) 3 ; -CO-OCH 3 ), 3.65(s, 9H, -N- (CH 3 ) 3 ), 4.80 (s, H, -O-CH), 5.2 (s, H, -O-CH), 5.8 (d, J = 6.0 Hz, H, -CO-CH 2 -N-), 5.29 (s, H, -O-CH), 5.36 (d, J =5.6, 2H, -CO-CH 2 -N-), 5.57 (d, J =5.6, H, -CO-CH 2 -N-), 5.36 (s, H, -CO- CH 2 -N-), 5.76 (d, J = 7.6, 2H, -CO-CH 2 -N-). 3 C-NMR (CDCl 3, 00 MHz) δ: 2.0, 7.88, 2.77, 23.36, 24.87, 26.07, 27.26, 27.83, 30.64, 30.80, 3.28, 34.04, 34.4, 34.76, 37.95, 39.97, 4.83, 45.37, 46.55, 5.48, 53.93, 54.6, 54.28, 60.40, 62.4, 64.06, 73.0, 74.7, 77.23, 64.29, 64.92,
14 HRMS (ESI-MS): m/z (C 40 H 72 N 3 O 8 ) +3 calculated ; found (M) 3+ / , M 3+ Cl - /2 calculated ; found M 3+ Cl - / , M 3+ Cl 2- calculated ; found M 3+ Cl CA-PIP 3 : H-NMR (CDCl 3, 400 MHz) δ: 0.73 (s, 3H, -CH 3 ), 0.83 (d, J = 5.2, 3H, -CH 3 ), 0.93 (s, 3H, - CH 3 ), (steroid), 3.46 (s, 3H, -N-CH 3 ), 3.50 (s, 3H, -N-CH 3 ), 3.53 (s, 3H, -N-CH 3 ), 3.6 (s, 3H, -CO-OCH 3 ), (m, 2H, 3 -CH 2 -N-CH 2 -), 4.79 (m, H, -CO-CH 2 -N-), 4.95 (d, J = 7.2 Hz, 2H, -O-CH), 5.53 (d, J =7.2 Hz, H, -CO-CH 2 -N-), 5.09 (s, 3H, -CO-OCH 3 ), 5.29 (s, 3H, H, -O- CH; -CO-CH 2 -N-), 5.32 (d, J =7.2 Hz, H, -CO-CH 2 -N-), 5.53 (d, J =7.2 Hz, H, -CO-CH 2 -N-), 5.70 (d, J = 7.2 Hz, H, -CO-CH 2 -N-), 5.77 (d, J =7.2 Hz, H, -CO-CH 2 -N-). 3 C-NMR (CDCl 3, 00 MHz) δ: 2.03, 7.89, 2., 2.30, 2.35, 2.42, 2.69, 2.79, 23.39, 24.97, 26., 27.3, 27.77, 30.6, 30.78, 3.36, 34.07, 34.47, 34.77, 37.98, 40.83, 45.34, 46.52, 47.65, 48.9, 5.48, 62.69, 62.90, 64.54, 64.97, 65.37, 65.50, 72.95, 74.9, 77.24, 77.62, 64.82, 65.39, 65.39, HRMS (ESI- MS): m/z (C 49 H 84 N 3 O 8 ) 3+ calculated ; found (M) 3+ / , M 3+ Cl - /2 calculated ; found M 3+ Cl - / CA-PYR 3 : H-NMR (CDCl 3, 400 MHz) δ: 0.72 (s, 3H, -CH 3 ), 0.90 (s, 6H, 2 X -CH 3 ), (steroid), 3.64 (s, 3H, -CO-OCH 3 ), 4.66 (m, H, -O-CH), 5.05 (m, H, -O-CH), (m, 2H, -CO- CH 2 -N-), (m, 2H, -CO-CH 2 -N-), (m, 2H, -CO-CH 2 -N-), 8.0 (m, 2H, ArH), 8.6 (m, 2H, ArH), 8.43 (m, 2H, ArH), 8.44 (m, H, ArH), 8.62 (m, H, ArH), 8.93 (m, H, ArH), 9.52 (s, 3H, ArH), 8.6 (s, 3H, ArH). 3 C-NMR (CDCl 3, 00 MHz) δ: 2.25, 7.76, 2.99, 23.2, 25.53, 26.9, 26.44, 27., 28.49, 29.67, 30.49, 3.5, 3.34, 34.04, 34.7, 34.40, 34.76, 37.73, 40.30, 42.6, 42.53, 45.45, 46.8, 5.54, 60.70, 6.6, 74.2, 77.26, 78.24, 27.6, 27.8, 28.77, 45.47, 45.87, 46.36, 46.7, 46.92, 47.02, 64.80, 65.8, 65.99, HRMS (ESI-MS): m/z (C 46 H 60 N 3 O 8 ) 3+ calculated ; found (M) 3+ / , M 3+ Cl - /2 calculated ; found M 3+ Cl - /
15 CA-DMAP 3 : H NMR (CDCl 3, 400 MHz) δ: 0.72 (s, 3H, -CH 3 ), 0.82 (d, J =5.2 3H, -CH 3 ), δ: 0.90 (s, 3H, -CH 3 ) (steroid), 3.9 (s, 6H, -N(CH 3 ) 2 ), 3.25 (s, 6H, -N(CH 3 ) 2 ), 3.3 (s, 6H, -N(CH 3 ) 2 ), 3.63 (s, 3H, -CO-OCH 3 ), 4.66 (m, H, -O-CH), 5.04 (s, H, -O-CH), 5.23 (s, H, -O-CH), 5.55 (m, H, -CO-CH 2 -N-), 5.88 (m, 3H, -CO-CH 2 -N-; -CO-CH 2 -N-), 6.84 (d, J =7.2 Hz, 2H, ArH), 6.94 (d, J = 6.8 Hz, 2H, ArH), 7.20 (d, J =7.2 Hz, 2H, ArH), 8.56 (d, J =7.2 Hz, 2H, ArH), 8.87 (s, 2H, ArH), 8.87 (s, 2H, ArH). 3 C-NMR (CDCl 3, 00 MHz) δ: 2.09, 7.679, 22.09, 23.2, 25.06, 26.2, 27.25, 28.4, 29.68, 30.53, 3.20, 34.00, 34.22, , 34.88, 37.97, 40.36, , 40.63, 42.35, 45.29, 46.9, 5.52, 57.67, 63.03, , 77.27, 07.42, 07.60, 08.06, 43.64, 44.06, 44.7, 56.33, 56.44, 56.53, 67.3, 67.43, 67.58, HRMS (ESI-MS): m/z (C 52 H 75 N 6 O 8 ) 3+ calculated ; found (M) 3+ / , M 3+ Cl - /2 calculated ; found M 3+ Cl - /
16 H, LCA-AMM 6
17 H, LCA-TMA 7
18 H, LCA-PIP 8
19 H, LCA-PYR 9
20 H, LCA-DMAP 20
21 H, CDCA-AMM 2 2
22 H, CDCA-TMA 2 22
23 H, CDCA-PIP 2 23
24 H, CDCA-PYR 2 24
25 H, CDCA-DMAP 2 25
26 H, DCA-AMM 2 26
27 H, DCA-TMA 2 27
28 H, DCA-PIP 2 28
29 H, DCA-PYR 2 29
30 H, DCA-DMAP 2 30
31 H, CA-AMM 3 3
32 32
33 H, CA-PIP 3 33
34 H, CA-PYR 3 34
35 H, CA-DMAP 3 35
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