A facile synthesis of N-Z/Boc-protected 1,3,4-oxadiazole-based peptidomimetics employing peptidyl thiosemicarbazides

Lamani, Ravi S.; Nagendra, G.; Sureshbabu, Vommina V.

doi:10.1016/j.tetlet.2010.07.004

Cited by 21 publications

(8 citation statements)

References 40 publications

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“…17 The installation of 1,3,4-oxadiazole was accomplished by nucleophilic addition of different hydrazides 11 to isothiocyanate 10 and subsequent intramolecular cyclization (Table 3). 18 Of note is that this two-step transformation could be performed in tandem without isolation of the corresponding thiosemicarbazide 12 in one pot. For example, a suspension of pyrazine-2-carbohydrazide (11a, 0.28 g, 2.03 mmol) in tetrahydrofuran (3 mL) was treated with isothiocyanate 10 (0.46 g, 2.09 mmol) at room temperature for 12 hours to give a clear yellow solution that was diluted by tetrahydrofuran (25 mL) and treated with p-toluenesulfonyl chloride (0.85 g, 4.46 mmol) and pyridine (0.63 mL, 7.79 mmol) at the same temperature for 24 hours to give oxadiazole 13a (0.44 g, 1.35 mmol) in 67% isolated yield.…”

Section: Figure 1 Important Bioactive Benzoxaborolesmentioning

confidence: 99%

A Convenient and Efficient Synthesis of Dipeptidyl Benzoxaboroles and Their Peptidomimetics

Tong

et al. 2013

Synthesis

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We have developed a convenient and efficient method for the synthesis of dipeptidyl benzoxaboroles and their peptidomimetics. The novel dipeptidyl benzoxaboroles were obtained by the protecting-group-free coupling of 6-amino-1,3-dihydro-2,1-benzoxaborol-1-ol with various N-(arylcarbonyl)phenylalanines. Bioisosteric replacement of the terminal amide moiety of dipeptidyl benzoxaboroles by 1,3,4-oxadiazoles or 4H-3,1-benzothiazin-4-one provided their peptidomimetics with good molecular diversity. These transformations were based on the pluripotency of methyl (S)-2-isothiocyanato-3-phenylpropanoate and were highlighted by mild reaction conditions, high atom efficiency, and good to excellent isolated yields. This method is a valuable addition to the development of novel drug-like boronic acid molecules.

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Section: Figure 1 Important Bioactive Benzoxaborolesmentioning

confidence: 99%

A Convenient and Efficient Synthesis of Dipeptidyl Benzoxaboroles and Their Peptidomimetics

Tong

et al. 2013

Synthesis

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“…It was observed that the higher temperature and presence of aromatic or electron withdrawing groups were necessary for effective deselenizaton/cyclization and longer reaction time up to 24 h was required for the cyclization at lower temperatures. In continuation of our studies on desulfurization/ deselenization using iodine reagents for the synthesis of 2‐amino‐1,3,4‐oxadiazoles,, we describe a novel I 2 mediated synthesis of 2‐iminohydantoins and 2‐amino‐1H‐imidazol‐4(5H)‐ones from selenourea tethered amides/peptides.…”

Section: Introductionmentioning

confidence: 99%

Molecular‐Iodine‐Mediated, Efficient One‐Pot Synthesis of 2‐Iminohydantoins and 2‐Amino‐1H‐imidazol‐4(5H)‐ones by Cyclodeselenization of Selenourea‐Tethered Amides/Peptides

et al. 2017

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An efficient one‐pot synthesis of 2‐iminohydantoins and 2‐amino‐1H‐imidazol‐4(5H)‐ones via iodine mediated intramolecular cyclodeselenization of intermediate selenourea tethered amides/peptides is described. The method employs selenophilic ability of environmentally benign iodine to effect the deselenization at room temperature, thereby avoids harsh conditions that are generally employed in the synthesis of iminohydantoins. Significantly 2‐(N‐alkylamino)‐1H‐imidazol‐4(5H)‐ones and 2‐iminohydantoin conjugates of di‐ and tripeptides could be synthesized. Other advantages of the method include mild condition, short duration, wide substrate scope, simple workup and purification of the products.

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“…Furthermore, the synthesis of derivatives containing an additional amino acid-derived substituent attached to the exocyclic amino group has been reported [15].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Crystal Structure of Benzyl [(1S)-1-(5-amino-1,3,4-oxadiazol-2-yl)-2-phenylethyl]carbamate

2012

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Abstract:The conversion of Z-phenylalanine hydrazide with cyanogen bromide resulted in the formation of the corresponding 2-amino-1,3,4-oxadiazole by spontaneous cyclization of the intermediary cyanohydrazide. The molecular structure of the product was confirmed by single crystal X-ray diffraction. Crystals of the title compound where obtained from a saturated solution in a mixture of petroleum ether and ethyl acetate and belong to the monoclinic space group P2 1 with unit cell parameters a = 9.8152(2) Å, b = 9.6305(2) Å, c = 9.8465(2) Å, β = 116.785(1)°. The asymmetric unit contains one molecule.

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A facile synthesis of N-Z/Boc-protected 1,3,4-oxadiazole-based peptidomimetics employing peptidyl thiosemicarbazides

Cited by 21 publications

References 40 publications

A Convenient and Efficient Synthesis of Dipeptidyl Benzoxaboroles and Their Peptidomimetics

A Convenient and Efficient Synthesis of Dipeptidyl Benzoxaboroles and Their Peptidomimetics

Molecular‐Iodine‐Mediated, Efficient One‐Pot Synthesis of 2‐Iminohydantoins and 2‐Amino‐1H‐imidazol‐4(5H)‐ones by Cyclodeselenization of Selenourea‐Tethered Amides/Peptides

Synthesis and Crystal Structure of Benzyl [(1S)-1-(5-amino-1,3,4-oxadiazol-2-yl)-2-phenylethyl]carbamate

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