Z-L-threonine hydrazide
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Z-L-threonine hydrazide

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Category
CBZ-Amino Acids
Catalog number
BAT-003379
CAS number
49706-30-1
Molecular Formula
C12H17N3O4
Molecular Weight
267.30
Z-L-threonine hydrazide
IUPAC Name
benzyl N-[(2S,3R)-1-hydrazinyl-3-hydroxy-1-oxobutan-2-yl]carbamate
Synonyms
Z-L-Thr-NHNH2; Benzyl ((2S,3R)-1-Hydrazinyl-3-Hydroxy-1-Oxobutan-2-Yl)Carbamate
Purity
≥ 98% (HPLC)
Melting Point
193-200 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C12H17N3O4/c1-8(16)10(11(17)15-13)14-12(18)19-7-9-5-3-2-4-6-9/h2-6,8,10,16H,7,13H2,1H3,(H,14,18)(H,15,17)/t8-,10+/m1/s1
InChI Key
KBPKTOXMTUBNDU-SCZZXKLOSA-N
Canonical SMILES
CC(C(C(=O)NN)NC(=O)OCC1=CC=CC=C1)O
1. Cyanoacetohydrazides in Synthesis of Heterocyclic Compounds
Hajar Hosseini, Mohammad Bayat Top Curr Chem (Cham). 2018 Oct 11;376(6):40. doi: 10.1007/s41061-018-0218-z.
Use of cyanoacetohydrazides as precursors in reactions leading to construction of heterocycles is reviewed. In addition to some common heterocyclic compounds, synthesis of other uncommon heterocycles such as thiadiazole, oxadiazole, fused heterocycles, and some seven- and eight-membered heterocycles such as benzodiazepine, oxazepine, and benzoxocine starting with cyanoacetohydrazides and their derivatives is also reported. The main aim of this review is to show the application of cyanoacetohydrazides in heterocyclic synthesis via different types of reaction, including cyclocondensation and cyclization. The results are arranged in terms of the type of heterocycle formed, from five-, six-, seven-, to eight-membered and fused rings. This review aims to cover literature up to 2018, showing the distribution of publications involving use of cyanoacetohydrazides for preparation of heterocycles.
2. Searching for novel antimicrobial agents among hydrazide-hydrazones of 4-iodosalicylic acid
Łukasz Popiołek, Katarzyna Tuszyńska, Anna Biernasiuk Biomed Pharmacother. 2022 Sep;153:113302. doi: 10.1016/j.biopha.2022.113302. Epub 2022 Jun 17.
Searching for novel antimicrobial agents is up to day topic for many group of researchers due to the fact that each year the number of bacterial strains resistant to currently used medicines increases. Special attention in the scientific literature among various groups of bioactive organic compounds is focused on the antimicrobial activity of hydrazide-hydrazones. Due to this fact presented study is focused on the design, synthesis and in vitro antimicrobial properties of novel hydrazide-hydrazones of 4-iodosalicylic acid. Target compounds were synthesized by the condensation reaction of the hydrazide of 4-iodosalicylic acid with substituted (hetero)aromatic aldehydes. Chemical structure of obtained molecules was confirmed by spectral methods (1H NMR and 13C NMR). Bioactivity screening results revealed interesting antimicrobial properties of tested compounds against reference Gram-positive bacteria and fungi belonging to Candida spp. Especially, hydrazide-hydrazones 3-5 showed very strong or strong bactericidal effect towards some cocci and bacilli (MIC = 7.81-15.62 µg/mL).
3. Cytotoxic benzylidene hydrazides of terephthalic acid and related compounds
M Hossain, S C Hall, P J Wiggington, S M Roth, S Das, U Das, P K Roayapalley, J R Dimmock Pharmazie. 2022 Apr 10;77(3):90-94. doi: 10.1691/ph.2022.11072.
The present investigation involved the synthesis of a number of novel benzylidene hydrazides as candidate cytotoxic agents. The preparation of these compounds from terephthalic acid and isophthalic acid proceeded satisfactorily. However, the reaction of phthalic acid hydrazide with various aryl aldehydes was unsuccessful in general. Some of the unexpected products were identified. The shapes and also the distances between the centers of the aryl rings designated B and C of three representative compounds 1b, 2b and 3b were determined. The compounds designated 1a-e, 2a-e and 3b were screened against human HCT116 and HT29 colon cancer cells as well as human CRL1790 non-malignant colon cells which revealed the tumor-selective toxicity displayed by these compounds.
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