Topic
Hydrazone
About: Hydrazone is a research topic. Over the lifetime, 4853 publications have been published within this topic receiving 65160 citations. The topic is also known as: hydrazone.
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TL;DR: In this paper, a typical opioid peptide sequence is combined with a fragment characteristic for neurokinin-1 receptor (NK1R) antagonists through a hydrazone bridge, which has a high affinity for μ- and δ-opioid receptors (IC50= 12.7 and 74.0 nM, respectively) and a weak affinity for the NK1R.
Abstract: The area of multitarget compounds, joining two pharmacophores within one molecule, is a vivid field of research in medicinal chemistry. Not only pharmacophoric elements are essential for the design and activity of such compounds, but the type and length of linkers used to connect them are also crucial. In the present contribution, we describe compound 1 in which a typical opioid peptide sequence is combined with a fragment characteristic for neurokinin-1 receptor (NK1R) antagonists through a hydrazone bridge. The compound has a high affinity for μ- and δ-opioid receptors (IC50= 12.7 and 74.0 nM, respectively) and a weak affinity for the NK1R. Molecular modeling and structural considerations explain the observed activities. In in vivo test, intrathecal and intravenous administrations of 1 exhibited a strong analgesic effect, which indicates potential BBB penetration. This letter brings an exemplary application of the hydrazone linker for fast, facile, and successful preparation of chimeric compounds.
21 citations
TL;DR: In this paper, the reaction of 2-hydroxybenzaldehydes with alkanols in the presence of triphenylphosphine and di-tert-butyl azodicarboxylate (DBAD), under the Mitsunobu reaction conditions, gives rise to the formation of hydrazones as the major products rather than the expected alkyl aryl ethers.
21 citations
TL;DR: The synthesis of a double hydrazone capable of undergoing photochemical E/Z isomerization through the imine double bonds is reported, introducing for the first timedouble hydrazones as tunable photochemical switches.
Abstract: Herein, we report the synthesis of a double hydrazone capable of undergoing photochemical E/Z isomerization through the imine double bonds. The bis(hydrazone) 1-E,E can be considered as a "two-arm" system in which the controlled movement of each arm is obtained by photo-modulation, making possible the appearance of two isolable metastable isomeric states 1-E,Z and 1-Z,Z. Such states are characterized by very specific structural, optical, and electrochemical properties. The latter allows the reversible return from either 1-E,Z or 1-Z,Z to the 1-E,E state. Our results are of great importance in the further development of molecular machines and photochemically controlled reactions by introducing for the first time double hydrazones as tunable photochemical switches.
21 citations
21 citations
TL;DR: A series of hydrazone and 3-nitrovinyl analogs of indole-3-carboxaldehydes and related compounds were synthesized and screened for antitubercular activity against Mycobacterium tuberculosis H37RV in BACTEC 12B medium using the Microplate Alamar Blue Assay (MABA).
Abstract: A series of hydrazone and 3-nitrovinyl analogs of indole-3-carboxaldehydes and related compounds were synthesized and screened for antitubercular activity against Mycobacterium tuberculosis H37RV in BACTEC 12B medium using the Microplate Alamar Blue Assay (MABA) Several compounds showed inhibitory activity against M tuberculosis in primary screening assays at a concentration of 625 μg/mL; subsequent dose-response studies indicated that the most active compounds, 3d, 3e & 8b, had IC50 values of 596, 54 & 16 μg/mL, respectively These compounds represent potential leads for the further development of novel antitubercular agents
21 citations