By Iwao Ojima, Edison S. Zuniga (auth.), Bimal K. Banik (eds.)
I. Ojima • E. S. Zuniga • J. D. Seitz: Advances within the Use of Enantiopure β-Lactams for the Synthesis of Biologically lively Compounds of Medicinal Interests.- I. Fernández • Miguel A. Sierra: β -Lactams from Fischer Carbene Complexes: Scope, barriers, and response Mechanism.- Bablee Mandal • Basudeb Basu: Synthesis of β-Lactams via Alkyne–Nitrone Cycloadditions.- T. T. Tidwell: education of Bis-β-Lactams by way of Ketene–Imine Cycloadditions.- Edward Turos: The Chemistry and Biology of N-Thiolated β-Lactams.- Indrani Banik • Bimal okay. Banik: Synthesis of β-Lactams and Their Chemical Manipulations through Microwave-Induced Reactions.
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Additional resources for β-Lactams: Unique Structures of Distinction for Novel Molecules
0]cyclobutane 134 as intermediates. Then, 134 undergoes C–N bond cleavage and ring contraction to form aziridine oxonium salt 135, which reacts with methoxide ion to give 130 (Scheme 38) . In the course of an attempt to synthesize a fused tricyclic system containing b-lactams, 3,4-difunctionalized b-lactam 136 was treated with DBU to give Advances in the Use of Enantiopure b-Lactams for the Synthesis of. . t. 2 44 - 70% 141 N R2 142 NR3 CN R1 R3N H CN N O R1 R1 = MeO, BnO R2 = PMP, Bn, allyl O R3 = PMP, p -tolyl, 4-Cl-C6H4, 4-Me2 N-C6H4 R2 143 NR3 CN NR2 146 NHR3 R1 O CN N R2 144 R1 O NHR3 CN NR2 145 Scheme 40 Cyanide-catalyzed ring-expansion of 4-imino-b-lactam via 1,4-bond cleavage and recyclization R1O O N O 147 R2 1.
T. t. TIPSO CF3 TIPSO N O PMP (-)-227 CF3 N PMP (+)-228 O PMP (-)-228 Scheme 67 Synthesis of enantiopure 3-TIPSO-4-trifluoromethyl-b-lactams via enzymatic optical resolution of racemic 3-acetoxy-b-lactam were obtained through enzymatic resolution of racemic cis-3-acetyl-4-CF3-b-lactam (Æ)-225, and converted to 3-TIPSO-b-lactams, (þ)- and (À)-228 (Scheme 67) [12, 50]. The PMP group of the enantiopure 4-Rf-b-lactams was removed by cerium ammonium nitrate (CAN) and the resulting NH-free b-lactams 229 were reacted with acyl chlorides, chloroformates, and arenesulfonyl chlorides in the presence of an appropriate base to give the corresponding N-acyl-, N-carbalkoxy, and Narenesulfonyl-b-lactams, 230, 231, and 232, in good yields (Scheme 68) .
The incorporation of fluorine(s) into a biologically active compound often improves the pharmacological properties of the compound, resulting in increased membrane permeability, enhanced hydrophobic binding, and stability against metabolic oxidation among other benefits [49, 120, 121]. In addition, fluorine is not present in living tissue. Thus, the addition of fluorine(s) into biologically active compounds as marker(s) for 19F NMR studies provides a simple and valuable means to monitor protein structures and drug–protein interactions in vitro and in vivo.
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