Hydrazine Moiety Research Articles

Metal-Free, PPA-Mediated Fisher Indole Synthesis via Tandem Hydroamination-Cyclization Reaction between Simple Alkynes and Arylhydrazines.

A new variant of Fisher indole synthesis involving Bronsted acid-catalyzed hydrohydrazination of unactivated terminal and internal acetylenes with arylhydrazines is reported. The use of polyphosphoric acid alone either as the reaction medium or in the presence of a co-solvent appears to provide the required balance for activating the C-C triple bond towards the nucleophilic attack of the hydrazine moiety without unrepairable reactivity loss of the latter due to competing amino group protonation. Additionally, the formal hydration of acetylenes to the corresponding ketones occurs under the same conditions, making it an alternative approach for generating carbonyl groups from alkynes.

Developing double-crosslinking 3D printed hydrogels for bone tissue engineering

Bone defects are one of the main causes of disability worldwide. Due to the disadvantages associated with autografts, the latest advances have been focused on tissue regeneration approaches that use injectable hydrogels or 3D printed hydrogel-based structures that could refill appropriately the bone gap area without the need for external fixatives, leading to bone formation in the long term. Injectable hydrogels could be applied in extrusion-based 3D printing as inks; in this sense, double-crosslinking hydrogels appear as ideal candidates. In this work, injectable and printable double crosslinkable hydrogels based on oxidized xanthan gum (XGox) and methacrylate polyaspartylhydrazide (PAHy-MA) were produced. The formation of dynamic hydrazone bonds, occurring between aldehyde groups on the polysaccharide backbone and hydrazine moieties of PAHy-MA, induced an instant gelation, conferring, also, injectability and self-healing properties to the hydrogels. The presence of methacrylic moieties on the synthetic polymer allowed further crosslinking upon UV irradiation that stabilized the hydrogel shape and mitigated its susceptibility to hydrolytic degradation. Obtained hydrogels showed pseudoplastic behaviour and good recovery of viscoelastic properties over time. The physicochemical and rheological characterization highlighted increased stability and higher viscoelastic moduli after photo-crosslinking. The hydrogels also showed good printability, cytocompatibility and the early formation of a bone-like matrix when osteosarcoma-derived cells (MG-63) were cultured in the scaffolds for 21 days, with an increased collagen I deposition, mineralization and the expression of characteristic osteogenic markers.

The Hydrazine Moiety in the Synthesis of Modified Nucleosides and Nucleotides.

Synthetic nucleoside mimics are re-emerging as crucial contenders for antiviral and anticancer medications. While, Ribavirin stands out for its unique antiviral properties, predominantly associated with its distinctive triazole heterocycle as a nucleobase, the exploration of alternative nitrogen-based aromatic heterocycles hold great promises for the discovery of novel bioactive nucleoside mimics. Although nucleoside derivatives synthesized from hydrazine-ribose units have been in development for many decades, they have been little evaluated biologically and even less for their antiviral properties. With the aim of taking a closer look at these under-explored derivatives and investigating their synthetic pathways, this review provides an overview of the molecular design, the chemical synthesis, and the biological activity, when available, of these nucleoside analogues. Overall, the entire body of work already done motivates further exploration of these analogues and encourages us of formulating structurally novel nucleoside drug candidates featuring innovative mode of action.

A highly sensitive Golgi-targeted fluorescent probe for the simultaneous detection of malondialdehyde and formaldehyde in living systems and foods

Malondialdehyde (MDA) and formaldehyde (FA) are highly active carbonyl substances widely present in both biological and abiotic systems. The detection of MDA and FA is of great significance for disease diagnosis and food safety monitoring. However, due to the similarity in structural properties between MDA and FA, very few probes for synergistically detecting MDA and FA were reported. In addition, functional abnormalities in the Golgi apparatus are closely related to MDA and FA, but currently there are no fluorescent probes that can detect MDA and FA in the Golgi apparatus. Therefore, we constructed a simple Golgi-targetable fluorescent probe GHA based on hydrazine moiety as the recognition site to produce a pyrazole structure after reaction with MDA and to generate a CN double bond after reaction with FA, allowing MDA and FA to be distinguished due to different emission wavelengths during the recognition process. The probe GHA has good specificity and sensitivity. Under the excitation of 350 nm, the blue fluorescence was significantly enhanced at 424 nm when the probe reacted with MDA, and the detection limit was 71 nM. At the same time, under the same excitation of 350 nm, the reaction with FA showed a significant enhancement of green fluorescence at 520 nm, with a detection limit of 12 nM for FA. And the simultaneous and high-resolution imaging of MDA and FA in the Golgi apparatus of cells was achieved. In addition, the applications of the probe GHA in food demonstrated it can provide a powerful method for food safety monitoring. In summary, this study offers a promising tool for the synergistic identification and determination of MDA and FA in the biosystem and food, facilitating the revelation of their detailed functions in Golgi apparatus and the monitoring of food safety.

Using ‘designer’ coherences to control electron transfer in a model bis(hydrazine) radical cation: can we still distinguish between direct and superexchange mechanisms?

We have simulated two mechanisms, direct and superexchange, for the electron transfer in a model Bis(hydrazine) Radical Cation, which consists of two hydrazine moieties coupled by a benzene ring. The computations, that are inspired by the attochemistry approach, focus on the electron dynamics arising from a coherent superposition of four cationic states. The electron dynamics, originating from a solution of the time dependent Schrödinger equation within the Ehrenfest method, is coupled to the relaxation of the nuclei. Both direct (ca. 15 fs dynamics) and superexchange (ca. 2 fs dynamics) mechanisms are observed and turn out to lie on a continuum depending on the strength of the coupling of the benzene bridge electron dynamics with the hydrazine chromophore dynamics. This contrasts with the chemical pathway approach where the direct mechanism is completely non-adiabatic via a conical intersection, while the superexchange mechanism involves an intermediate radical with the unpaired electron localized on the benzene ring. Thus, with the attochemistry-inspired electron dynamics approach, one can distinguish direct from superexchange mechanisms depending on the strength of the coupling of two types of electron dynamics: the slow hydrazine dynamics (ca. 15 fs) and the fast benzene linker dynamics (ca. 2 fs). In this model bis(hydrazine) radical cation, only when the intermediate coupler is in an anti-quinoid state, does one see the coupling of the bridge and hydrazine chromophore dynamics.

Metal‐triggered supramolecular hydrogels based on bipyridine ligand possessing hydrazine moieties with metal ions

AbstractBipyridine‐based gelator 1 having two D‐alanine units was prepared, and its gelation ability was evaluated in the presence of Co(NO3)2 and AgNO3 in water. Gelator 1 could gelate H2O in the presence of Co(NO3)2 or AgNO3 (1.0 equiv.) in water. Gelator 1 formed a 2:1 (1:Co2+) octahedral complex with Co2+, whereas it formed a 2:1 (1:Ag+) tetrahedral complex with Ag+. The metallosupramolecular hydrogel with Co2+ assembled into a left‐handed helical fiber, whereas that with Ag+ assembled into a nanorod structure. 1H NMR and FTIR analyses revealed that π–π stacking and intermolecular hydrogen bonds acted as the driving force for the formation of the supramolecular nanoarchitectures. Furthermore, to characterize the viscoelastic properties of hydrogels, rheology experiments were conducted at 25°C, including time, strain, and frequency sweeps.

Versatile Structural Engineering of Metal-Organic Frameworks Enabling Switchable Catalytic Selectivity.

The structure engineering of metal-organic frameworks (MOFs) forms the cornerstone of their applications. Nonetheless, realizing the simultaneous versatile structure engineering of MOFs remains a significant challenge. Herein, a dynamically mediated synthesis strategy to simultaneously engineer the crystal structure, defect structure, and nanostructure of MOFs is proposed. These include amorphous Zr-ODB nanoparticles, crystalline Zr-ODB-hz (ODB = 4,4'-oxalyldibenzoate, hz = hydrazine) nanosheets, and defective d-Zr-ODB-hz nanosheets. Aberration-corrected scanning transmission electron microscopy combined with low-dose high-angle annular dark-field imaging technique vividly portrays these engineered structures. Concurrently, the introduced hydrazine moieties confer self-reduction properties to the respective MOF structures, allowing the in situ installation of catalytic Pd nanoparticles. Remarkably, in the hydrogenation of vanillin-like biomass derivatives, Pd/Zr-ODB-hz yields partially hydrogenated alcohols as the primary products, whereas Pd/d-Zr-ODB-hz exclusively produces fully hydrogenated alkanes. Density functional theory calculations, coupled with experimental evidence, uncover the catalytic selectivity switch triggered by the change in structure type. The proposed strategy of versatile structure engineering of MOFs introduces an innovative pathway for the development of high-performance MOF-based catalysts for various reactions.

Design, Synthesis and Anti-Bacterial Activity Evaluation of Indole-Based Benzophenone and Their Derivatives

Indole and benzophenone moiety are of significant interest to investigators because they are found in many natural products and pharmacologically active compounds. They represent versatile synthetic building blocks. The benzophenone and indole scaffolds are special structures in medicinal chemistry because these compounds are found in several biologically active natural products, compounds containing indole and benzophenone exhibit anticancer, antiinflammatory, antimicrobial, and antiviral activities. In this study, derivatives of 2-(diphenyl methylene) hydrazine, containing both indole and benzophenone moieties were successfully synthesized. The structural elucidation of the synthesized compounds were done using spectroscopic techniques like IR, 1HNMR, and 13CNMR. The synthesized target compounds were investigated for their in vitro antibacterial activity against two bacterial strains; staphylococcus aureus (S. auras), and Escherichia coli (E. coli) using the disc diffusion method. All synthesized target compounds showed no significant activity against Staphylococcus aureus (S. aureus) but exhibited moderate activity against Escherichia coli (E. coli). Among all the synthesized compounds, 2-(diphenyl methylene)-1-((1-tosyl-1H-indol-3-yl) methylene) hydrazine (BHT) (7b) showed a good inhibition at a concentration of 50 μg/mL with a zone of inhibition of 21.7 mm against Escherichia coli (E.coli) which was comparable with standard drug Ceftriaxone with the zone of inhibition of 26 mm. Thus, this compound could be considered as a lead molecule to design and develop novel antibacterial drugs.

Synthesis of 4-(1-(2-(2,4-dinitrophenyl)hydrazineylidene)-5-phenylpenta-2,4-dien-1-yl)-1-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazole as optical sensor for the toxic heavy metal ions in an aqueous medium

Heavy metal ions represented as highly toxic pollutants for the environment. In the search for new optical sensors for heavy metals, here, new organic linker [4-(1-(2-(2,4-dinitrophenyl)hydrazineylidene)-5-phenylpenta-2,4‑dien-1-yl)-1-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazole] was prepared in 87% yield by simple and facile method. The techniques of synthesis follow the formation of chalcone then condensation with hydrazine moiety to perform hydrazone derivatives. It was synthesized from addition of 1-(1-(4-Methoxyphenyl)-5-methyl-1H-1,2,3-triazol-4-yl)-5-phenylpenta-2,4‑dien-1-one to 2,4-dinitrophenylhdrazine. The chemical structure of prepared linker was established by the IR and NMR spectral data in addition to single-crystal X-ray crystallography. The new linker was used for detection of various metal ions (Cu2+, Zn2+, Cr3+, Co2+, Cd2+, and Hg2+). Interestingly, the new linker showed highly detection level and selectivity toward Hg2+ions. The color of the Hg2+ ions solution was turned from colorless to green when adding the title compound performed excellent naked-eye detection. The binding stoichiometry of the linker to the Hg2+ ions was found to be 1:1, which was confirmed by Job plot. For industrial application, the new linker was mixed with filter paper and used for detection of Hg2+ions. The new fabricated filter paper was identified using scanning electron microscopy (SEM). The present fabricated filter paper produced naked eye colorimetric detection of Hg2+ions.

Synthesis and Structural Investigations of 1, 2-bis(2-ethoxybenzylidene)hydrazine

The titled compound, 1,2-bis(2-ethoxybenzylidene) hydrazine was developed using the reaction of 2-ethoxybenzaldehyde and hydrazine monohydrate in an ethanolic solution. In the Schiff-based hydrazine compound, C18H20N2O2, the mid-point of the nitrogen atoms of the central hydrazine moiety is located in inversion symmetry. In C18H20N2O2, C−H···N hydrogen bond linked the molecules, and the framework stabilized by weak C−H···π and π···π stacking interactions. MEP, HOMO and LUMO analysis were performed with the DFT/B3LYP method and the 6-311+G(d,p) basis set. The energies of frontier orbitals were calculated to understand specific molecular properties such as electronegativity, chemical reactivity, chemical hardness and softness. For investigating the contributions of various intermolecular contacts within the hydrazine compound, Hirshfeld surface analysis was performed. The largest contribution of the compound to the main interactions comes from the H···H (64%), C···H (16%) and N···H (9%) interactions.

Structure-based drug design, synthesis, and biological evaluation of novel 1,3,5-triazine or pyrimidine derivatives containing benzoyl hydrazine moiety as PI3Kα selective inhibitors

Phosphoinositide 3-kinase (PI3K) was an important cellular signal transducer, while PI3Kα was the most mutated family member in cancer. Selective PI3Kα inhibitors have become the frequent research in recent years because of their excellent curative effect and reduced side effects. Here, we described a series of PI3Kα inhibitors with 1,3,5-triazine or pyrimidine skeleton containing benzoyl hydrazine based on the pan-PI3K inhibitor ZSTK474 relying on the strategies of structure-based drug discovery (SBDD) and computer-aided drug design (CADD). Among them, compound F8 exhibited improved selective PI3Kα inhibition with an IC50 value of 0.14 nM and more significant anti-proliferative activities against three tumor-derived cell lines (PC-3 IC50 = 0.28 μM, HCT-116 IC50 = 0.57 μM, and U87-MG IC50 = 1.37 μM) than ZSTK-474. Compound F-8 induced a great decrease in mitochondrial membrane which caused cell cycle arrest at G1 phase and apoptosis in U87-MG cells in a dose-dependent manner. Furthermore, compound F8 induced significant tumor regressions in a xenograft mouse model of U87-MG cell line with no clear evidence of toxicity following intraperitoneal injection of 40 mg/kg. Compound F8 may serve as a PI3Kα-selective inhibitor and provided the opportunity to spare patients the side effects associated with broader inhibition of the class I PI3K family.

Novel pyrazole-4-carboxamides and aromatic carboxamides derivatives containing a hydrazine moiety as potential SDHIs

To promote the discovery and development of novel SDHIs fungicides, a series of novel pyrazole-4-carboxamides 4a-t and aromatic carboxamides 8a-i with a hydrazine scaffold were designed, synthesized, and evaluated for their antifungal activities. The results showed that compound 4i exhibited outstanding antifungal activity against R. solani with EC50 value of 0.24 μg/mL, which was about three times more potent than that of Boscalid (EC50 = 0.74 μg/mL). Moreover, compound 4i also displayed promising antifungal activities against Sclerotinia sclerotiorum, B. cinerea, Alternaria alternate, and F. graminearum (IC50 = 1.21–4.50 μg/mL), indicating a broad spectrum of antifungal activities. Additionally, in vivo antifungal activities results showed that 4i could significantly inhibit the growth of R. solani in rice leaves with good protective efficacy (55.21%) and excellent curative efficacy (73.06%) at 100 μg/mL. The results of the SDH enzymatic inhibition assay showed that compound 4i generated significant SDH inhibition with IC50 value of 6.47 μM, which was superior to Boscalid (IC50 = 7.92 μM). Furthermore, SEM analysis showed that compound 4i could remarkably disrupt the typical structure and morphology of R. solani hyphae. The molecular docking study revealed that compound 4i could form H-bonds interactions and π-π interactions with TRP173 and TRY58 at the activity site of SDH, which was similar to that of Boscalid. The DFT calculation provided crucial information regarding electron transfer, which was essential in understanding the mechanism of molecules and target enzymes. These results indicated that compound 4i showed potential as a SDHIs fungicide and warranted further investigation.

Design, Synthesis, and Bioactivity of Aldisine Derivatives Containing Oxime and Hydrazine Moieties Based on Hydrogen Bonds.

Marine natural products have attracted more and more attention in drug research and development due to their unique structure, diverse biological activities, and novel mode of action. Using antiviral alkaloid aldisine as the lead compound and drawing on the hydrogen bond effect widely used in drug design, derivatives containing oxime and hydrazone moieties were designed and synthesized by introducing functional groups with hydrogen-bond receptors or donors into molecules. The configuration of derivatives was systematically studied through nuclear Overhauser effect (NOE) spectroscopy and single crystal analysis. The antiviral activity test result showed that most derivatives had antiviral activity against tobacco mosaic virus (TMV), and some compounds had better activity than the commercial antiviral drug ribavirin, especially compounds 2 and 24, which had comparable activity to the most effective commercial antiviral drug ningnanmycin. Preliminary mode of action studies showed that compound 2 could affect the assembly of rod-shaped TMVs by promoting the aggregation and fragmentation of TMV coat proteins. Molecular docking experiments demonstrated that the introduction of oxime and hydrazone moieties could indeed increase the hydrogen bond between molecules and target proteins. In addition, we conducted fungicidal and larvicidal activities study of these derivatives. Most of these derivatives had good larvicidal activities against Mythimna separata and Plutella xylostella and showed broad-spectrum fungicidal activities.

Antifungal Properties of Hydrazine-Based Compounds against Candida albicans.

Candida albicans, an opportunistic yeast, is the most common cause of fungal infection. In the past decade, there has been an increase in C. albicans resistance to existing antifungal drugs, which has necessitated the development of new antifungal agents. In the present study, screening 60 compounds from the JUNIA chemical library enabled us to explore an additional 11 hybrid compounds that contain pyrrolidinone rings and hydrazine moieties for their potential antifungal activities. This chemical series was identified with fair to excellent antifungal activities. Among this series, three molecules (Hyd.H, Hyd.OCH3, and Hyd.Cl) significantly reduced C. albicans viability, with rapid fungicidal activity. In addition, these three compounds exhibited significant antifungal activity against clinically isolated fluconazole- or caspofungin-resistant C. albicans strains. Hyd.H, Hyd.OCH3, and Hyd.Cl did not show any cytotoxicity against human cancer cell lines up to a concentration of 50 µg/mL and decreased Candida biofilm formation, with a significant reduction of 60% biofilm formation with Hyd.OCH3. In an infection model of Caenorhabditis elegans with C. albicans, hydrazine-based compounds significantly reduced nematode mortality. Overall, fungicidal activity was observed for Hyd.H, Hyd.OCH3, and Hyd.Cl against C. albicans, and these compounds protected C. elegans from C. albicans infection.

Design and synthesis of a new bifunctional chelating agent: Application for Al 18F/177Lu complexation

Theranostic and personalized medicine are blooming strategies to improve oncologic patients' health care and facilitate early treatment. While 18F-radiochemistry for theranostic application is attractive due to its imaging properties, combining diagnosis by positron emission tomography (PET) via aluminum-fluoride-18 and β− therapy with lutetium-177 is relevant. Nevertheless, it requires the use of two different chelating agents, which are NOTA and DOTA for aluminum-fluoride-18 and lutetium-177 radiolabeling, respectively. To overcome this issue, we propose herein the synthesis of a new hybrid chelating agent named NO2A-AHM, which can be labeled with different types of emitters (β+, β− and γ) using the mismatched Al18F/177Lu pair. NO2A-AHM, is based on a hydrazine moiety functionalized by a NOTA cycle, a chelating arm, and a linker with a maleimide function. This design is chosen to increase the flexibility and allow the formation of 5 up to 7 coordination bonds with metal ions. Moreover, this agent can be coupled to targeting moieties containing a thiol function, such as peptides, to increase selectivity towards specific cancer cells. Experimental complexation and computational chemistry studies are performed to confirm the capacity of our chelating agent to label both aluminum-fluoride and lutetium using molecular modeling approaches at Density Functional Theory (DFT) level.The proof of concept of the ability of NO2A-AHM to complex both aluminum-fluoride-18, for PET imaging applications, and lutetium-177 for radiotherapy has shown encouraging results which is prominent for the development of a fully consistent theranostic approach.

Design and Synthesis of 2-(4-Bromophenyl)Quinoline-4-Carbohydrazide Derivatives via Molecular Hybridization as Novel Microbial DNA-Gyrase Inhibitors.

Microbial DNA gyrase is regarded as an outstanding microbial target. Hence, 15 new quinoline derivatives (5-14) were designed and synthesized. The antimicrobial activity of the afforded compounds was pursued via in vitro approaches. The investigated compounds displayed eligible MIC values, particularly against G-positive Staphylococcus aureus species. Consequently, an S. aureus DNA gyrase supercoiling assay was performed, using ciprofloxacin as a reference control. Obviously, compounds 6b and 10 unveiled IC50 values of 33.64 and 8.45 μM, respectively. Alongside, ciprofloxacin exhibited an IC50 value of 3.80 μM. Furthermore, a significant docking binding score was encountered by compound 6b (-7.73 kcal/mol), surpassing ciprofloxacin (-7.29 kcal/mol). Additionally, both compounds 6b and 10 revealed high GIT absorption without passing the blood brain barrier. Finally, the conducted structure-activity relationship study assured the usefulness of the hydrazine moiety as a molecular hybrid for activity either in cyclic or opened form.

A white light emitting single halochromic hydrazine bridged bis(3-pyrrolyl BODIPY) fluorophore.

In search of white light emitting fluorophores, a hydrazine bridged Schiff base compound, bis(3-pyrrolyl BODIPY), was synthesized by condensing readily available α-formyl 3-pyrrolyl BODIPY with hydrazine hydrate in CH3OH under reflux for 5 h followed by recrystallization. Bis(3-pyrrolyl BODIPY) was thoroughly characterized by HR-MS, 1D and 2D NMR, and X-ray crystallography. The X-ray structure revealed that the 3-pyrrolyl BODIPY units in the dyad were arranged trans to each other with respect to the hydrazine moiety. Bis(3-pyrrolyl BODIPY) showed absorption bands in the region of 390-705 nm and exhibited multiple fluorescence bands in the region of 395-720 nm at different excitation wavelengths. The protonated derivative of bis(3-pyrrolyl BODIPY) generated by the addition of TFA to its CH2Cl2 solution showed significant changes in the optical properties and generated white fluorescence under UV light with specific emission bands observed in blue, green, and red regions, indicating that bis(3-pyrrolyl)BODIPY is a single white light emitting halochromic fluorophore under acidic conditions. DFT and TD-DFT studies justify the structural and electronic properties of the protonated derivative of bis(3-pyrrolyl BODIPY) exhibiting white light emission.

Synthesis and Antitrypanosomal and Mechanistic Studies of a Series of 2-Arylquinazolin-4-hydrazines: A Hydrazine Moiety as a Selective, Safe, and Specific Pharmacophore to Design Antitrypanosomal Agents Targeting NO Release.

Nitric oxide (NO) represents a valuable target to design antitrypanosomal agents by its high toxicity against trypanosomatids and minimal side effects on host macrophages. The progress of NO-donors as antitrypanosomal has been restricted by the high toxicity of their agents, which usually is based on NO-heterocycles and metallic NO-complexes. Herein, we carried out the design of a new class of NO-donors based on the susceptibility of the hydrazine moiety connected to an electron-deficient ring to be reduced to the amine moiety with release of NO. Then, a series of novel 2-arylquinazolin-4-hydrazine, with the potential ability to disrupt the parasite folate metabolism, were synthesized. Their in vitro evaluation against Leishmania and Trypanosoma cruzi parasites and mechanistic aspects were investigated. The compounds displayed significant leishmanicidal activity, identifying three potential candidates, that is, 3b, 3c, and 3f, for further assays by their good antiamastigote activities against Leishmania braziliensis, low toxicity, non-mutagenicity, and good ADME profile. Against T. cruzi parasites, derivatives 3b, 3c, and 3e displayed interesting levels of activities and selectivities. Mechanistic studies revealed that the 2-arylquinazolin-4-hydrazines act as either antifolate or NO-donor agents. NMR, fluorescence, and theoretical studies supported the fact that the quinazolin-hydrazine decomposed easily in an oxidative environment via cleavage of the N-N bond to release the corresponding heterocyclic-amine and NO. Generation of NO from axenic parasites was confirmed by the Griess test. All the evidence showed the potential of hydrazine connected to the electron-deficient ring to design effective and safe NO-donors against trypanosomatids.

Ulcer Index, Analgesics and Anti inflammatory Screening of Some Arylidene Compounds Derived from Phenyl Hydrazine and Aromatic Aldehydes

Arylidene derivatives were synthesized from phenyl hydrazine and series of different aldehydes. Arylidene compounds are important classes of N-containing fused heterocycles widely used as key building blocks for pharmaceutical agents due to a wide range of biological activities that include anti-inflammatory and antitumor properties [1]. Arylidene derivatives were furnished by the fusion of benzene ring with different aldehydes via hydrazine moiety in the presence of glacial acetic acid. These derivatives were characterized by TLC, melting points, Infrared Red, Nuclear Magnetic Resonance and Mass Spectroscopy. Finally, these synthetized derivatives were tested for analgesic activity using hot plate test method, anti-inflammatory activity using rat paw oedema and ulcer index test.

Design, Synthesis, and Bioactivities of Novel Tryptophan Derivatives Containing 2,5-Diketopiperazine and Acyl Hydrazine Moieties.

Based on the scaffolds widely used in drug design, a series of novel tryptophan derivatives containing 2,5-diketopiperazine and acyl hydrazine moieties have been designed, synthesized, characterized, and evaluated for their biological activities. The bioassay results showed that the target compounds possessed moderate to good antiviral activities against tobacco mosaic virus (TMV), among which compounds 4, 9, 14, 19, and 24 showed higher inactivation, curative, and protection activities in vivo than that of ribavirin (39 ± 1, 37 ± 1, 39 ± 1 at 500 mg/L) and comparable to that of ningnanmycin (58 ± 1, 55 ± 1, 57 ± 1% at 500 mg/L). Thus, these compounds are a promising candidate for anti-TMV development. Most of these compounds showed broad-spectrum fungicidal activities against 13 kinds of phytopathogenic fungi and selective fungicidal activities against Alternaria solani, Phytophthora capsica, and Sclerotinia sclerotiorum. Additionally, some of these compounds exhibited larvicidal activities against Tetranychus cinnabarinus, Plutella xylostella, Culex pipiens pallens, Mythimna separata, Helicoverpa armigera, and Pyrausta nubilalis.