Dibrompropamidine → Pentamidine

HRID 551575Notes

Reaction equation

HRID 551575 reaction equation
C1C(C(N)=N)=CC=C(O[CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]([NH2:23])=[NH:22])=[CH:19][CH:20]=2)C=1.[CH:24]1[C:29]([C:30]([NH2:32])=[NH:31])=[CH:28][C:27](Br)=[C:26]([O:34][CH2:35][CH2:36]COC2C=CC(C(N)=N)=CC=2Br)[CH:25]=1.C1C(C(N)=N)=CC=C(OCCCCCCOC2C=CC(C(N)=N)=CC=2)C=1>N[C@H](C(O)=O)CC(C)C>[CH:28]1[C:29]([C:30]([NH2:32])=[NH:31])=[CH:24][CH:25]=[C:26]([O:34][CH2:35][CH2:36][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([NH2:23])=[NH:22])=[CH:17][CH:16]=2)[CH:27]=1

Participants

5

Reactant 3

HCID 11974DibrompropamidineHCID 64949PropamidineHCID 65130Hexamidine

Product 1

HCID 4735Pentamidine

Reagents, catalysts & solvents 1

HCID 6106L-LeucineSolvent

Procedure

Efflux pump inhibitory activity of propamidine, dibromopropamidine, and hexamidine was confirmed in Leu-Nap accumulation assays. The uptake of Leu-Nap (100 μg/ml) by PAM1723 (FIGS. 10A, C, and E) or PAM1626 (FIGS. 10B, D, and F) cells was studied in the presence of various concentrations of propamidine (0 μg/ml to 160 μg/ml), dibromopropamidine (0 to μg/ml to 40 μg/ml), and hexamidine (0 μg/ml to 40 μg/ml), respectively. All three compounds were capable of completely inhibiting the MexAB-OprM-mediated efflux of Leu-Nap from the strain overexpressing this pump. The rate of Leu-NAp uptake into PAM1626, and PAM1723, in the presence of 160 μg/ml propamidine, 20 μg/ml of dibromoproapmidine, and 20 μg/ml of hexamidine was the same.

Workup

  1. concentrationThe uptake of Leu-Nap (100 μg/ml) by PAM1723 (FIGS. 10A, C, and E) or PAM1626 (FIGS. 10B, D, and F) cells was studied in the presence of various concentrations of propamidine (0 μg/ml to 160 μg/ml), dibromopropamidine (0 to μg/ml to 40 μg/ml), and hexamidine (0 μg/ml to 40 μg/ml)

Sources & evidence

ORD record
ord-09a8fefec27a47cebbe9baaf376991ce
Source dataset
uspto-grants-2011_05
Patent number
US07947741B2

Reaction notes

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