Synthesis of Some New (Nα-Dipicolinoyl)-bis-L-leucyl-DL-norvalyl Linear tetra and Cyclic octa Bridged Peptides as New Antiinflammatory Agents

2003 ◽  
Vol 58 (9) ◽  
pp. 903-910 ◽  
Author(s):  
Mohamed H. Abo-Ghalia ◽  
Abd El-Galil E. Amr ◽  
Mohamed M. Abdalah
Keyword(s):  
Methyl Ester ◽  
Structure Elucidation ◽  
Ulcer Formation ◽  
Significant Activity ◽  
Paw Edema ◽  
Antiinflammatory Drugs ◽  
Mass Spectral Analysis ◽  
Mass Spectral ◽  
Antiinflammatory Agents ◽  
New Compounds

In continuation to our search for new amino acid and peptide based anti-inflammatory agents, the suggestion, synthesis, structure elucidation of some Nα -bis-dipicolinoyl amino acids, linear tetra and cyclic octa bridged peptides 1-9, of which four are new compounds 6-9, were herein realized. Accordingly, Nα -bis-dipicolinoyl-L-leucine methyl ester 1, the corresponding acid 2, its bis-DL-norvalyl methyl ester homologue 3, the acid 4 and hydrazide 5 analogues were conventionally prepared.The tetrachlorophthalic acid hydrazine conjugate 6, anisaldehyde hydrazone 7, the benzenetetracarboxylic acid and naphthalenetetracarboxylic acid bis-L-leucyl-DL-norvalyl cyclic octa bridged peptides 8 and 9 respectively, were newly synthesized via condensation of the hydrazide 5 with the corresponding aldehyde or anhydride.The chromatographic, IR, NMR and mass spectral analysis confirmed the identities of the synthesized compounds.Comparable to the two reference antiinflammatory drugs indomethacin® and voltaren® (100%), the determined antiinflammatory potency of the candidates (carrageenan® induced paw edema in rats) revealed a general significant activity (66 - 94%), except for the practically inactive 6 (∼1.5 % activity).In particular, the potency of the (Nα -dipicolinoyl)-bis-L-leucyl-DL-norvalyl anisaldehyde hydrazone 7 was of 94 and 87%, comparable to the reference drugs. However, 7 also showed 58% protection against ulcer formation, comparable to null for indomethacin®. Additionally, an acceptable acute toxicity was observed (LD50: 2833 mg/kg, comparable to 2700 and 2850 for indomethacin® and voltaren® respectively).

scholarly journals Isolation of New Secondary Metabolites from New Zealand Marine Invertebrates

2021 ◽  
Author(s):  
◽  
Joanna M Wojnar
Keyword(s):  
New Zealand ◽  
Methyl Ester ◽  
Secondary Metabolites ◽  
Chromatographic Separation ◽  
Structure Elucidation ◽  
Screening Tool ◽  
Marine Invertebrates ◽  
Toxic Metabolites ◽  
The Family ◽  
New Compounds

<p>This study describes the isolation and structure elucidation of several known and 13 new compounds from New Zealand marine organisms. Furthermore, it describes the development of a digital mask program for the analysis of HSQC spectra of crude sponge extracts. This was used as a screening tool to identify secondary metabolite producers that warranted further analysis. As reports of metabolites from New Zealand nudibranchs are poorly represented in the literature, a study of five New Zealand nudibranch species was undertaken. These coloured and seemingly undefended nudibranchs are known to concentrate or sequester toxic metabolites from their prey, facilitating rapid isolation and structure elucidation of these metabolites. This study resulted in the isolation of a variety of metabolite classes; two new compounds, 13alpha- acetoxypukalide diol (30) and lopholide diol (31) from the nudibranch Tritonia incerta, are described. Examination of the sponge Raspailia agminata resulted in the isolation of a novel family of partially acetylated glycolipids which contain up to six glucose residues. The chromatographic separation of these compounds was a challenge due to the similarity of the congeners and their lack of a chromophore. MSguided isolation eventually led to the purification of agminosides A-E (145-149). An unidentified sponge of the order Dictyoceratida was found to contain a new isomer (186) of the known sesterterpene variabilin. As variabilin-type compounds are predominantly found from sponges of the family Irciniidae, the unidentified sponge is most likely an irciniid. In addition, the sponge contained two prenylated quinones, one of which, 189, is a new isomer of a known sponge metabolite. The sponge Darwinella oxeata contained four new nitrogenous diterpenes of the aplysulphurane (rearranged spongian) skeleton, oxeatamide A (214), isooxeatamide A (215), oxeatamide A 23-methyl ester (216) and oxeatamide B (217).</p>

scholarly journals Prenylated Xanthones and a Benzophenone from Baphia Kirkii

2008 ◽  
Vol 3 (9) ◽  
pp. 1934578X0800300 ◽  
Author(s):  
Modest C. Kapingu ◽  
Joseph J. Magadula
Keyword(s):  
Spectral Analysis ◽  
Ethanol Extract ◽  
Mass Spectral Analysis ◽  
Mass Spectral ◽  
New Compounds

From the ethanol extract of the whole stem of Baphia kirkii, three new prenylated xanthones, baphikixanthones A-C, have been isolated together with a new benzophenone, baphikinone, and two common steroids, stigmasterol and β–sitosterol. The structures of the new compounds were established by using NMR spectroscopic and mass spectral analysis.

scholarly journals Syntheses of 3,3-Disubstituted Dihydrobenzofurans, Indolines, Indolinones and Isochromanes by Palladium-Catalyzed Tandem Reaction Using Pd(PPh3)2Cl2/(±)-BINAP as a Catalytic System

Catalysts ◽  
2020 ◽  
Vol 10 (9) ◽  
pp. 1084
Author(s):  
Guizhou Yue ◽  
Sicheng Li ◽  
Dan Jiang ◽  
Gang Ding ◽  
Juhua Feng ◽  
...  
Keyword(s):  
Catalytic System ◽  
General Procedure ◽  
Tandem Reaction ◽  
Isomer Ratio ◽  
Spectroscopic Techniques ◽  
Mass Spectral Analysis ◽  
1H And 13C Nmr ◽  
Mass Spectral ◽  
Palladium Catalyzed ◽  
New Compounds

A general procedure for the tandem arylation reaction of arylbromide with heteroaryl compounds was developed by using Pd(PPh3)2Cl2/(±)-BINAP (1,1′-Binaphthalene-2,2′-diylbis (diphenylphosphane)) as catalytic system. Both sulphur- and oxygen-containing heterocycles were also employed as an efficient reagent for arylation, which gave moderate to excellent yields with moderate to good regioselectivities (5:1 to > 20:1 ir (isomer ratio)). Except for dihydrobenzofurans, indolines and indolinones, this type of tandem reaction was also expanded to synthesize isochromanes. The synthesized new compounds were well characterized through different spectroscopic techniques, such as 1H and 13C NMR (nuclear magnetic resonance), and mass spectral analysis.

scholarly journals Synthesis and Anti-Inflammatory Activity of a Novel Series of Diphenyl-1,2,4-triazoles and Related Derivatives

2012 ◽  
Vol 9 (4) ◽  
pp. 2510-2515 ◽  
Author(s):  
Swapna Cherala ◽  
Harikiran Lingabathula ◽  
Rama Ganta ◽  
Srinivas Ampati ◽  
Sarangapani Manda
Keyword(s):  
Spectral Analysis ◽  
Rat Model ◽  
Inflammatory Activity ◽  
Paw Edema ◽  
Mass Spectral Analysis ◽  
Thiourea Derivatives ◽  
Mass Spectral ◽  
H Nmr ◽  
Anti Inflammatory

In the present investigation we have synthesized a series of new 1-[3-(4-substitutedphenyl)-5-phenyl-4H-1,2,4-triazol-4-yl]urea and 1-[3-(4-substitutedphenyl)-5-phenyl-4H-1,2,4-triazol-4-yl]thiourea derivatives (4Ia - 4IId). The newly synthesised derivatives were characterized by using the data of IR,1H NMR and Mass Spectral analysis. Thus synthesised and characterized targetted compounds were further screened for their anti-inflammatory activity by using Carrageenan – induced paw edema rat model. Among all the newly synthesized derivatives, Compounds 4Ia-4Ic and Compounds 4IIa-4IId were reduced the inflammation very significantly (p<0.0001), thus these compounds showed promising anti-inflammatory activity and only one compound (4Id) showed moderate anti-inflammatory activity (p<0.05).

scholarly journals Synthesis and Anti-inflammatory Activity of Some Novel 2,4-Diaryl-3,5-bis(arylimino)-1,2,4-thiadiazolidine Derivatives

2009 ◽  
Vol 6 (2) ◽  
pp. 495-503 ◽  
Author(s):  
P. Venkatesh ◽  
S. N. Pandeya
Keyword(s):  
Diclofenac Sodium ◽  
Inflammatory Activity ◽  
Second Step ◽  
Paw Edema ◽  
Mass Spectral Data ◽  
Mass Spectral ◽  
Methoxy Groups ◽  
Anti Inflammatory ◽  
Sar Study ◽  
New Compounds

A series of some novel 2,4-diaryl-3,5-bis(arylimino)-1,2,4-thiadiazolidine derivatives were synthesized and evaluated for anti-inflammatory activity. In the SAR study, the phenyl ring on 3 and 4 position of 1,2,4-thiadiazolidine ring substituted with chloro, nitro and methoxy groups showed better activity. The title compounds were synthesized from two steps; the first step involved the synthesis of diaryl substituted thioureas then, it was cyclised to give the 1,2,4-thiadiazole system in the presence of oxidizing agent (hydrogen peroxide and concentrated hydrochloric acid) in the second step. The purity of the synthesized compounds were judged by their C, H and N analysis and the structure was analyzed on the basis of IR, H1NMR, C13NMR and Mass spectral data. The anti-inflammatory activity of new compounds was determined by λ-Carrageenan induced mice paw edema method using diclofenac sodium as a standard. Among the compounds tested four compounds, B2 (2,4-diphenyl-3,5-bis(3-nitrophenylimino)-1,2,4-thiadiazolidine), B4 (2,4-diphenyl-3,5-bis(3-chlorophenylimino)-1,2,4-thiadiazolidine), B6 (2,4-diphenyl-3,5-bis(4-methoxyphenylimino)-1,2,4-thiadiazolidine) and B7 (2,4-diphenyl-3,5-bis (2-methoxyphenylimino)-1,2,4-thiadiazolidine) were the most active compounds in these series.

scholarly journals Isolation of New Secondary Metabolites from New Zealand Marine Invertebrates

2021 ◽  
Author(s):  
◽  
Joanna M Wojnar
Keyword(s):  
New Zealand ◽  
Methyl Ester ◽  
Secondary Metabolites ◽  
Chromatographic Separation ◽  
Structure Elucidation ◽  
Screening Tool ◽  
Marine Invertebrates ◽  
Toxic Metabolites ◽  
The Family ◽  
New Compounds

<p>This study describes the isolation and structure elucidation of several known and 13 new compounds from New Zealand marine organisms. Furthermore, it describes the development of a digital mask program for the analysis of HSQC spectra of crude sponge extracts. This was used as a screening tool to identify secondary metabolite producers that warranted further analysis. As reports of metabolites from New Zealand nudibranchs are poorly represented in the literature, a study of five New Zealand nudibranch species was undertaken. These coloured and seemingly undefended nudibranchs are known to concentrate or sequester toxic metabolites from their prey, facilitating rapid isolation and structure elucidation of these metabolites. This study resulted in the isolation of a variety of metabolite classes; two new compounds, 13alpha- acetoxypukalide diol (30) and lopholide diol (31) from the nudibranch Tritonia incerta, are described. Examination of the sponge Raspailia agminata resulted in the isolation of a novel family of partially acetylated glycolipids which contain up to six glucose residues. The chromatographic separation of these compounds was a challenge due to the similarity of the congeners and their lack of a chromophore. MSguided isolation eventually led to the purification of agminosides A-E (145-149). An unidentified sponge of the order Dictyoceratida was found to contain a new isomer (186) of the known sesterterpene variabilin. As variabilin-type compounds are predominantly found from sponges of the family Irciniidae, the unidentified sponge is most likely an irciniid. In addition, the sponge contained two prenylated quinones, one of which, 189, is a new isomer of a known sponge metabolite. The sponge Darwinella oxeata contained four new nitrogenous diterpenes of the aplysulphurane (rearranged spongian) skeleton, oxeatamide A (214), isooxeatamide A (215), oxeatamide A 23-methyl ester (216) and oxeatamide B (217).</p>

scholarly journals An efficient multicomponent synthesis of 1H-pyrano[2,3-d]pyrimidine-2,4(3H,5H)-dione derivatives and evaluation of their α-amylase and α-glucosidase inhibitory activity

2020 ◽  
pp. 174751982096404
Author(s):  
Mamata Devendra Naik ◽  
Yadav D Bodke ◽  
Prashantha J ◽  
Jayanth K Naik
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Enzyme Activity ◽  
Spectral Analysis ◽  
Spectroscopic Techniques ◽  
Multicomponent Synthesis ◽  
Mass Spectral Analysis ◽  
Mass Spectral ◽  
Inhibitory Potential ◽  
New Compounds

In this paper, we report the synthesis of novel 1 H-pyrano[2,3- d]pyrimidine-2,4(3 H,5 H)-dione derivatives 5(a–j) by a facile multicomponent reaction. The structures of all the newly synthesized compounds were characterized by different spectroscopic techniques including infrared, nuclear magnetic resonance (1H and 13C) and mass spectral analysis. All the new compounds were assessed for their in vitro α-amylase and α-glucosidase enzyme inhibitory potential. The results of the assays revealed that all compounds showed different enzyme inhibition activities. The concentration required to inhibit enzyme activity is less in the case of α-glucosidases than for α-amylases, that is, the synthesized compounds are more potent in arresting α-glucosidase enzyme activity.

scholarly journals Preparation and Characterization of New 1,3,5-Trisubstituted-2-Pyrazolines Derivative for their Anti-Inflammatory Activity

2021 ◽  
pp. 992-1004
Author(s):  
Jitendra Kumar Chaudhary ◽  
Alok Pal Jain ◽  
O. P. Tiwari
Keyword(s):  
Inflammatory Activity ◽  
Paw Edema ◽  
Mass Spectral Analysis ◽  
Phenyl Hydrazine ◽  
Design Synthesis ◽  
Standard Drug ◽  
Mass Spectral ◽  
Anti Inflammatory ◽  
Relevant Degree

The objective of the paper was to design, synthesis and characterization of new 1,3,5-trisubstituted-2-pyrazolines derivative and evaluate for anti-inflammatory potential. The 1,3,5-tri-substituted-2-pyrazolines derivatives has been synthesized by the reaction of chalcone     derivatives with 4-hydrazinylbenzene sulfonamide hydrochloride and phenyl hydrazine hydrochloride. Total Sixteen compounds has been synthesized and characterized by the IR, 1HNMR and mass spectral analysis. Proposed compounds have been evaluated for anti-inflammatory activity. Anti-inflammatory activity of the compounds carried out by two animal     model i.e. Carrageenan induced, paw edema in rats and Inhibition of formalin induced paw edema in rats. Anti-inflammatory activity of the compounds C7, C8 and C2 were shown 98.26,  92.77 and 96.24 percentages of inhibition and compounds D7, D8 and D2  were shown 81.50, 83.81 and 78.32 percentages of inhibition as compared to the standard drug Diclofenac at 10 mg/kg was inhibit the inflammation 99.42 % after 6h. These result is a evident that synthesized compounds show relevant degree of anti-inflammatory activity as compared to the standard drug. It is also concluded that the presence of SO2NH2 group, Cl, CH3, OCH3 and N(CH3)2 group may provide the active compounds when attached to the pyrazoline group. But the addition of OH, Br and no substitution in phenyl ring may diminish the activity. 

Effect of Nectaroscordum koelzi Methanolic Extract on Acute and Chronic Inflammation in Male Mice

2020 ◽  
Vol 20 ◽  
Author(s):  
Karam Hossein Hasanvand ◽  
Mojtaba Khaksarian ◽  
Maryam Alipour ◽  
Hormoz Mahmoudvand ◽  
Massumeh Naizi ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Chronic Inflammation ◽  
Acute Inflammation ◽  
Methanol Extract ◽  
Significant Activity ◽  
Paw Edema ◽  
Ear Edema ◽  
Edema Volume ◽  
Cotton Pellet ◽  
Acute And Chronic Inflammation

Introduction: The present study deals with the effect of Nectaroscordum koelzi fruit extract on acute and chronic inflammation. Methods: Totally, 84 NMRI mice were used in this study. The extract effect on acute inflammation was analyzed by increasing vascular permeability via acetic acid and xylene induced ear edema among mice. The extract was evaluated in terms of effects on chronic inflammation by means of the cotton pellet test among mice. For the assessment of inflammation degree, the mice paw edema volume was measured by the plethysmometric test. Results: The findings showed that the extract was effective on acute inflammation induced by acetic acid in mice. In the xylene ear edema, N. koelzi extract indicated the significant activity in mice. In the cotton pellet method, the methanol extract produced a significant reduction in comparison with the control and dexamethasone. Mice paw edema volume decreased with the extract. Conclusion: In general, the data from the experiments indicated that the methanol extract of N. koelzi has an anti-inflammatory effect on acute and chronic inflammation. However, the exact contributing mechanisms have not been investigated for the pharmacological effects.

scholarly journals SYNTHESIS, CHARACTERIZATION, AND ANTHELMINTIC ACTIVITY OF NOVEL BENZOTHIAZOLE DERIVATIVES CONTAINING INDOLE MOIETIES

2019 ◽  
pp. 321-325
Author(s):  
ALETI RAJAREDDY ◽  
SRINIVAS MURTHY M
Keyword(s):  
Spectral Analysis ◽  
Fourier Transform ◽  
Infrared Spectroscopy ◽  
Magnetic Resonance ◽  
Fourier Transform Infrared Spectroscopy ◽  
Anthelmintic Activity ◽  
Mass Spectral Analysis ◽  
Standard Drug ◽  
Mass Spectral ◽  
Benzothiazole Derivatives

Objective: The objective of this study was to synthesize and evaluate the anthelmintic activity (AA) of novel benzothiazole derivatives containing indole moieties (BDIM). Methods: The present works which involve the substituted isatin Schiff bases undergo acetylating and reacting with 2-aminobenzothiazole to give novel BDIM. Results: All the newly synthesized molecules (5a-5o) were characterized by Fourier-transform infrared spectroscopy, H_nuclear magnetic resonance, and mass spectral analysis along with physical data. The biological potentials of the newly synthesized compounds are evaluated for their AA using an Indian earthworm (Pheretima posthuma), and albendazole was used as standard drug. Conclusion: The synthesized compound 5f, 5n, and 5o showed good AA, whereas others exhibited significant activities.

Sign in / Sign up

Export Citation Format

Share Document