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Abstract

The purpose of the research was to synthesize hybrid molecules based on the imide group by preparing diazonium salts, perform coupling reactions for these salts, and study the biological activities of the synthesized compounds. Therefore, three innovative heterocyclic imide compounds (1, 2, 3) were synthesized by reacting 2-aminobenzothiazole with (phthalic anhydride, maleic anhydride, and 1,8-naphthalic anhydride) in the presence of ethanol. Following that, the compounds (5, 6, 7) were prepared by coupling of diazonium salts, which prepared by dissolving 2-aminobenzothiazole in a solution of concentrated hydrochloric acid and water at a temperature below 5 °C with different aldehydes (para-chlorobenzaldehyde, para-hydroxybenzaldehyde, and N, N-dimethylamine benzaldehyde) in the presence of a catalyst such as HCl and water as the solvent. The mixture was refluxed for 3 h at a temperature below 5 °C, and then allowed to cool, washed with water, filtered, and the precipitate collected. All prepared compounds were purified, and their structures were confirmed by spectroscopic methods such as Fourier transform infrared (FTIR) and proton nuclear magnetic resonance (¹H NMR). The biological activity of these compounds was studied and discussed against four types of bacteria (Gram-negative and Gram-positive), including Streptococcus pyogenes, Klebsiella pneumoniae, Escherichia coli, and Staphylococcus aureus. The obtained results were compared theoretically with other drugs (Sulfamethoxazole, Penicillin, Naproxen, and Ibuprofen). The new compounds (1, 2, 5, and 7) showed significant inhibition against various types of bacteria, with some effects surpassing those of the drugs, possibly due to the heterocyclic structures of the synthesized compounds.

Keywords

2-aminobenzothiazole antibacterial activities diazonium salts heterocyclic sulfonamide sulfamethoxazole

Introduction

There has been a steady increase in the synthesis of hybrid molecules and their evaluation as powerful medications and a variety of pharmacological agents.^1,2 In the fields of chemistry and medicine, the most common chemical work to develop modified scaffolds with several enhanced and remarkable features is hybrid molecules, which are produced by combining the structural characteristics of two differently active segments.^3,4 In general, these compounds are antibacterial against a variety of Gram-negative pathogenic bacteria.^5,6 It has been reported that several compounds with anticancer, antimalarial, antibacterial, antidiabetic, anti-inflammatory, and antioxidant effects are based on heterocyclic sulfonamide derivatives.^7,8

Sulfonamides are chemical compounds with a benzene ring S-linked to a distinctive nitrogen and sulfur dioxide group. The biological and pharmacological actions of sulfonamide and its derivatives have drawn a lot of attention.⁹ Sulfonamides are widely used substances with a wide range of applications in the literature.¹⁰

The promising antibacterial potential of sulfonamide derivatives against both Gram-positive and Gram-negative bacteria has been underlined by recent investigations (2022–2025).^11,12 Strong action against Klebsiella pneumoniae was demonstrated by sulfonamide-based indole derivatives, while azithromycin-sulfonamide conjugates improved efficacy against Streptococcus pyogenes-resistant bacteria.¹³ Against a variety of diseases, novel 7-methoxyquinoline sulfonamide compounds showed strong antibacterial and antibiofilm properties. Furthermore, broad-spectrum antibacterial properties were demonstrated by sulfonamides with oxyacetal and pyrimidine moieties. In addition, recent quinoline–sulfonamide hybrids demonstrated potent inhibitory activity against a variety of bacterial strains, highlighting the significance of structural alterations to enhance antibacterial efficiency. These results imply that sulfonamide derivatives continue to be a useful platform for creating novel antimicrobial medicines, particularly those that target resistant bacterial species.¹⁴

In the current treatment plan for sulfonamide therapy, prodrug sulfonamides are crucial.¹⁵ Sulfonyl succinyl, for example, acts as a prodrug of sulfathiazole. Because it ionized in the alkaline environment of the colon and was gradually hydrolyzed by gut enzymes, it was used to treat gut infections.¹⁶ The amide group increases the sulfonamide’s hydrophilic properties and decreases its polarity. It makes it easier for the medication to pass through the intestinal wall and be broken down by enzymes.¹⁷

In addition to their use in medicine, sulfonamide derivatives are widely used as dyes, plasticizers, corrosion inhibitors, and synthetic fibers.¹⁸ Similarly, antitumor and antiulcer medicines are made from benzene sulfonamide and its derivatives.¹⁹ Therefore, this study aimed to the preparation and characterization of hybrid functionality molecular-based varieties of heterocyclic rings and investigated their correlation between compound structures and their biological activities.

Material and methods

All the chemicals applied in our study are obtainable from Fluka. And for Sigma Aldrich, the melting points have been specified by Electro thermal capillary apparatus. Infrared spectra were obtained using the ATR technique Shimadzu 8400S, and Fourier Transform Infrared spectroscopy SHIMADZU in the range (400–4000) cm⁻¹. The ¹H-NMR spectra were obtained on a Bruker model ultra-shield 400 MHz in the laboratories of the University of Science and Technology (Tehran). Using tetra methyl silane (TMS) as an internal reference and DMSO-d6 as a solvent, mass spectrum analyses were performed by the Agilent Technology MS 5973 device.

Results and discussion

New compounds containing isoxazoles and benzothiazoles of heterocyclic rings have been synthesized successfully. Phthalic anhydride, maleic anhydride, and 1,8-naphthalic anhydride were used with 2-aminobenzothiazole as a starting material to prepare the target compounds.

To synthesize diazonium salts, two solutions were prepared: the first one containing of HCl dissolved in 2-aminobenzothiazole, and the second solution was sodium nitrite. The two solutions were mixed and stirred at 5 °C for 3 h. The end of the reactions was monitored by thin-layer chromatography (TLC). Then, the substituted benzaldehyde was added to obtain the target compounds (Scheme 1). The biological efficiency of the products was studied on four types of bacteria. They showed good biological activities toward Gram-positive and Gram-negative bacteria.

Scheme 1.

Synthesis route of cyclic imide compounds (1–3) and coupling of diazonium salts 4a with different benzaldehyde (5–7); (i) refluxed for 3 h at 100–110 °C; (ii) diazotization reaction at 5 °C for 6 h; and (iii) coupling reactions of diazonium salt, hexane, reflux, 3 h.

The prepared compounds were confirmed by Fourier transform infrared (FTIR) and ¹H NMR through the appearance of the amide carbonyl stretching vibration and the absence of carbonyl group which clearly supported the formation of the target compounds (Tables 1 and 2).²⁰ However, the structure of the compounds (5–7) which prepared after the coupling with a diazonium salts.²¹

Table 1.

FTIR spectrum data for cyclic imide derivatives (1–3).

Comp. no.	NH	C-H arom.	C-H alip.	C=N	C=O	C=C		SO₂
Comp. no.	NH	C-H arom.	C-H alip.	C=N	C=O			Asym	Sym
1	3373	3066	2992	1736	1636	1566	1460	1329	1265
2	3372	3066	2922	1700	1665	1585	1461	1330	1218
3	3370	3080	2995	1740	1702	1628	1453	1337	1229

Table 2.

FTIR spectrum data of coupling diazonium salts (5–7).

IR (K Br) cm⁻¹
Comp. no.	NH	C–H arom.	C–H alip.	C–H ald.	C=O	C=C		SO₂		C=N-	Others
Comp. no.	NH	C–H arom.	C–H alip.	C–H ald.	C=O			Asym	Sym	C=N-	Others
5	3230	3029	2916	2700	1625	1587	1470	1325	1260	1630	C–Cl 740
6	3232	3032	2930	2720	1630	1589	1485	1335	1227	1645	OH 3548
7	3240	3028	2918	2760	1638	1594	1498	1337	1230	1658	C–N 1337

Biological activity

The biological activity of the synthesized compounds was investigated by evaluating their effects on four bacterial species: two Gram-negative bacteria (E. coli and K. pneumoniae) and two Gram-positive bacteria (Staphylococcus aureus and S. pyogenes). Mueller-Hinton Agar (MHA) was used as the culture medium, which is commonly employed in determining the biological activities of antibiotics and chemical substances for medical use during the measurement of minimum inhibitory concentrations (MIC). The antibacterial activity data presented in Table 3 for the prepared compounds (1–7) were compared to standard drugs: Sulfamethoxazole, Naproxen, Ibuprofen, and Penicillin. The activity is expressed in zones of inhibition (in mm) against four bacterial strains: E. coli, S. aureus, S. pyogenes, and K. pneumoniae. Results are shown for three concentrations: 0.1%, 1%, and 10%.

Table 3.

Antibacterial activity data for compounds (1–7) sulfamethoxazole, naproxen, ibuprofen, penicillin.

Comp. no.	Conc.%	E. coli, mm	Staphylococcus aureus, mm	Streptococcus pyogenes, mm	K. pneumoniae, mm
1	0.1	8	18	12	10
	1	14	22	18	15
	10	18	28	24	20
2	0.1	5	5	3	8
	1	8	15	17	17
	10	17	25	30	25
3	0.1	1	5	5	9
	1	5	17	15	13
	10	10	22	28	20
4	0.1	1	5	5	5
	1	4	10	15	8
	10	8	15	28	10
5	0.1	5	5	5	5
	1	12	17	18	15
	10	25	27	32	30
6	0.1	3	5	5	8
	1	10	15	15	13
	10	20	24	29	20
7	0.1	2	5	5	5
	1	8	17	18	10
	10	17	30	35	15
Sulfamethoxazole	0.1	3	5	5	6
	1	8	8	10	13
	10	17	20	20	21
Naproxen	0.1	7	15	10	5
	1	10	20	15	10
	10	15	25	20	20
Ibuprofen	0.1	5	10	8	3
	1	8	15	12	6
	10	12	20	16	9
Penicillin	0.1	5	20	10	3
	1	10	25	15	5
	10	15	30	20	7

The antibacterial activity data reveal that among the synthesized compounds (1–7), compound 5 exhibited the most potent and broad-spectrum effect, with inhibition zones of 25 mm (E. coli), 27 mm (S. aureus), 32 mm (S. pyogenes), and 30 mm (K. pneumoniae) at 10% concentration surpassing standard drugs like penicillin and sulfamethoxazole in most cases. However, S. aureus and S. pyogenes are generally more sensitive across all tested compounds. The synthesized compounds 1, 2, 5, and 7 demonstrated a strong antibacterial activity to combat S. aureus, S. pyogenes, and K. pneumoniae (Figure 1). This effect was particularly notable at higher concentrations, indicating that their efficacy increases with the amount used.

Figure 1.

Antibacterial activity of the prepared compounds at 10% concentration.

Therefore, compound 5 is the most promising antibacterial agent, with the highest and broadest activity across the board. While the compounds 1, 2, and 7 also show strong and sometimes superior activity to standard antibiotics. These results warrant further pharmacological testing, including MIC, toxicity, and mechanism elucidation studies.

Besides, compound 7 also demonstrated strong activity, particularly against S. pyogenes (35 mm) and S. aureus (30 mm), while compound 1 showed balanced efficacy across all strains with zones ranging from 18 to 28 mm. Also, compound 2 was notably effective against S. pyogenes (30 mm) and K. pneumoniae (25 mm), indicating good Gram-positive targeting.²² In contrast, compound 4 was the least effective, with inhibition zones not exceeding 15 mm. The data clearly show a dose-dependent response, and several compounds displayed superior inhibition zones compared to the reference drugs, suggesting that compounds 1, 2, 5, and 7 hold promising potential as novel antibacterial agents. However, the inhibition zone increases as concentration increases from 0.1% to 10%.

Moreover, some of these compounds outperformed conventional drugs in combating certain bacterial species, as shown in Table 3 and Figure 2. In the study of biological activity, a comparison was made between various drugs and the synthesized compounds. Sulfamethoxazole demonstrated good efficacy at a 10% concentration against all bacterial species, with a particularly strong effect against K. pneumoniae (21 mm), surpassing most of the synthesized compounds. Naproxen exhibited moderate activity against S. aureus and S. pyogenes at the same concentration, but its impact on E. coli and K. pneumoniae was lower compared to the synthesized compounds. On the contrary, ibuprofen generally showed weak efficacy in comparison to the other drugs and synthesized compounds. Penicillin displayed strong activity against S. aureus at a 10% concentration (30 mm), although its effect on K. pneumoniae was less pronounced compared to the other drugs.

Figure 2.

Biological activity of the prepared compounds: (a) compound 1 inhibits the growth of bacteria E. coli; (b) compound 2 inhibits the growth of bacteria E. coli; (c) compound 7 inhibits the growth of S. pyogenes; and (d) compound 5 inhibits the growth of K. pneumoniae.

Experimental section

General procedure for synthesis of compound (1–3)

A mixture of compound 7 (1.55 g, 0.005 mol) was combined with maleic anhydride (0.49 g, 0.005 mol), phthalic anhydride (0.74 g, 0.005 mol), and 1,8-naphthalic anhydride (0.99 g, 0.005 mol) and refluxed at 100–110 °C for 3 h. The mixture was then cooled, washed, and recrystallized from ethanol to obtain the products (1–3).

2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-(5-methylisoxazol-3-yl)benzo[d]thiazole-6-sulfonamide (1)

Bright yellow solid; yield: 1.53 g (75%); m.p. = 155–157 °C. ¹H NMR (400 MHz, CDCl₃) spectrum signal appeared at δ 8.3–7.8 (m, 3H, benzothiazole), δ -6.50 (s, 2H, pyrrole -2,5-dion (C=O), 6.10 (s, H, isoxazol). FTIR (KBr): 1636 cm⁻¹ (C=O), 1736 cm⁻¹ (C=N), 3066 cm⁻¹ (C–H, ArH), 2992 cm⁻¹ (C–H, alip.H), 1566–1460 cm^-1 (C=C).

2-(1,3-dioxoisoindolin-2-yl)-N-(5-methylisoxazol-3-yl)benzo[d]thiazole-6-sulfonamide (2)

Dark-yellow solid; yield: 78%, m.p. = 162–164 °C. FTIR (KBr): 1700 cm⁻¹ (C=N), 1665 cm⁻¹ (C=O), 3066 cm⁻¹ (C–H, ArH), 2992 cm⁻¹ (C–H, alip.H), 1585–1461cm^-1 (C=C).

2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)-N-(5-methylisoxazol-3-yl)benzo[d]thiazole-6-sulfonamide (3)

Orange solid; yield: 80%, m.p. = 174–176 °C. (KBr): 1636 cm⁻¹ (C=O), 1736 cm⁻¹ (C=N), 3066 cm⁻¹ (C–H, ArH), 2992 cm⁻¹ (C–H, alip.H), 1566–1460 cm⁻¹ (C=C).

General procedure for synthesis of compounds (5–7)

Synthesis 2-(chlorodiazenyl)-N-(5-methylisoxazol-3-yl)benzo[d]thiazole-6-sulfonamide (4a)

Step 1: A mixture of compound 4 (0.93 g, 0.003 mole) was dissolved in 7 mL of concentrated acid HCl and 7 mL of water. The mixture was stirred in an ice bath at 5 °C. Then, 1.6 g of sodium nitrite was dissolved in 8 mL of water and stirred in an ice bath before being added to the first solution. The temperature of the reaction was kept below 5 °C for 6 h. The end of the reaction was monitored by TLC, and the product was washed and recrystallized to give compound 4. Yellow solid; yield: 85%, m.p. = 180–182 °C. FTIR (KBr): 1660 cm⁻¹ (C=N), 3030 cm⁻¹ (C–H, ArH), 2990 cm⁻¹ (C–H, alip.H), 1585–1461cm^-1 (C=C), 1335 cm⁻¹ (C–N).

Step 2: A mixture of compound 4a was combined with various benzaldehyde such as 4-chlorobenzaldehyde (0.42 g, 0.003 mol), 4-hydroxybenzaldehyde (0.37 g, 0.003 mol), and 4-(dimethylamino)benzaldehyde (0.45 g, 0.003 mol) to obtain compounds (5–7). The solution was reflux in the presence of hexane as a solvent for 3 h. Later, the mixture was cooled to room temperature, and the precipitate was filtered, washed with water, and recrystallized from solvent to give the product as follow:

2-((2-chloro-5-formylphenyl)diazenyl)-N-(5-methylisoxazol-3-yl)benzo[d]thiazole-6-sulfonamide (5)

Light-yellow solid, yield: 70%; m.p. = 166–168 °C . FTIR (KBr): 1630 cm⁻¹ (C=N), 1626 cm⁻¹ (C=O) 3029 cm⁻¹ (C–H, ArH), 2916 cm⁻¹ (C–H, alip.H), 1587–1470 cm^-1 (C=C) 2700 cm⁻¹ (C–H, ald.H), 740 cm⁻¹ (C–Cl).

2-((5-formyl-2-hydroxyphenyl)diazenyl)-N-(5-methylisoxazol-3-yl)benzo[d]thiazole-6-sulfonamide (6)

Yellow solid; yield: 80%; m.p. = 170–172 °C. FTIR (KBr): 1630 cm⁻¹ (C=N), 1626 cm⁻¹ (C=O), 3032 cm⁻¹ (C–H, ArH), 2930 cm⁻¹ (C–H, alip.H), 1589–1485 cm⁻¹ (C=C), 2720 cm⁻¹ (C–H ald.H), 3548 cm⁻¹ (C–OH).

((2-(dimethylamino)-5-formylphenyl)diazenyl)-N-(5-methylisoxazol-3-yl)benzo[d]thiazole-6-sulfonamide (7)

Dark-orange solid; yield: 83%; m.p. = 178–180 °C. ¹H NMR(400 MHz, CDCl₃) spectrum signal appeared as follows: δ 9.66 (s, 1H, C H=O), δ 7.72–7.66 (m, 3H, ArH), δ 2.96–2.5 (s, 6H, C H₃-N-CH₃₎, δ 2. (s, 3H, C H₃-C-O). FTIR (KBr): 1630 cm⁻¹ (C=N), 1626 cm⁻¹ (C=O), 3032 cm⁻¹ (C–H, ArH), 2930 cm⁻¹ (C–H, alip.H), 1589–1485 cm^-1 (C=C), 2720 cm⁻¹ (C–H ald.H), 3548 cm⁻¹ (C–OH).

Conclusion

The current study focuses on the synthesis and characterization of heterocyclic imide compounds, as well as the synthesis and characterization of dual diazonium salts based on 2-aminobenzothiazole. This was achieved in two stages. The first stage involves the synthesis of cyclic imide compounds through the reaction of 2-aminobenzothiazole with various cyclic anhydrides. The second stage includes the reaction of 2-aminobenzothiazole with an HCl solution diluted with distilled water at a 1:1 ratio and a sodium nitrite solution in an ice bath to obtain diazonium salt as an intermediate stage. This salt was then converted into a pair or conjugation by reacting with benzaldehyde derivatives. The prepared compounds were confirmed using spectroscopic methods, and their efficiency was demonstrated in inhibiting four types of bacteria, two of which are Gram-positive and two are Gram-negative. The compounds 1, 2, 5, and 7 demonstrated a strong ability to combat S. aureus and S. pyogenes bacteria. This effect was particularly noticeable when higher concentrations of these compounds were used, indicating that their efficacy increases with greater amounts. Furthermore, some of these compounds outperformed conventional drugs in combating certain bacterial species. This superiority suggests that these compounds could serve as effective alternatives to existing medications or could be used alongside known drugs to enhance their effectiveness against bacteria compared with some drugs such as sulfamethoxazole, naproxen, ibuprofen, and penicillin.

Supplemental Material

sj-docx-1-chl-10.1177_17475198251362960 – Supplemental material for Synthesis, characterization, and biological activity of some novel sulfonamide derivatives

Supplemental material, sj-docx-1-chl-10.1177_17475198251362960 for Synthesis, characterization, and biological activity of some novel sulfonamide derivatives by Bushra T Mahdi, Huda Turki Mahdi, Mohammed Hadi Ali Al-Jumaili and Malath Khalaf Rasheed in Journal of Chemical Research

Footnotes

Acknowledgements

The completion of this research paper would not have been possible without the support and guidance of the University of Anbar and the University of Fallujah. I would like to clarify that the H NMR spectra for compounds 1 and 7 are indeed included in the manuscript. These spectra provide detailed chemical shift assignments and were carefully processed and interpreted to support the structural claims. I trust they serve as representative examples that confirm the methodologies and analytical rigor applied throughout the study. I fully recognize that the absence of data of other compounds may limit the ability to independently verify the structural claims. While I have relied on detailed experimental notes, complementary analytical data (melting point and FTIR), and standard literature comparisons to support the structural assignments. While I acknowledge the limitations posed by the absence of raw data for some compounds, I hope that the inclusion of verified NMR spectra for compounds 1 and 7, along with the experimental details provided, sufficiently demonstrates the validity of the work performed.

ORCID iD

Mohammed Hadi Ali Al-Jumaili

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Funding

The author(s) received no financial support for the research, authorship, and/or publication of this article.

Declaration of Conflicting Interests

The author(s) declared no potential conflicts of interest with respect to the research, authorship, and/or publication of this article.

Data Availability Statement

The data that support this study are accompanying as a supplementary material.

Supplemental Material

Supplemental material for this article is available online.

References

Alkhzem

Woodman

Blagbrough

IS.

Design and synthesis of hybrid compounds as novel drugs and medicines. RSC Adv 2022; 12(30): 19470–19484.

Al-Jumaili

MHA

Bakr

Huessien

, et al. Development of heterocyclic-based anticancer agents: a comprehensive review. Heterocycl Commun 2025; 31(1): 20220179.

Farhan

Hussein

Al-Jumaili

MHA

. Synthesis, characterization, and biological activities investigation of tri-armed structure of (7-bromo-5-chloro-2,3-dihydrophthalazine-1,4-dione) based on benzene ring. J Chem Res 2024; 48(6): 17475198241306505.

Alazzawi

Al-Jumaili

MHA

. Novel spiroheterocycles containing a 1,3,4-thiadiazole unit: synthesis and spectroscopic characterization. J Chem Res 2022; 46(4): 17475198221109503.

Sadek

Mekheimer

Abd-Elmonem

, et al. Recent developments in the synthesis of hybrid heterocycles, a promising approach to develop multi-target antibacterial agents. J Mol Struct 2023; 1286: 135616.

Hussein

Al-Jumaili

MHA

Sabi

, et al. Indium-catalyzed direct amidation reaction of carboxylic acids and in silico study for screening the activity of potential therapeutics of the synthesized products. ChemistrySelect 2024; 9(37): e202403097.

Verma

Xue

, et al. Antibacterial activities of sulfonyl or sulfonamide containing heterocyclic derivatives and its structure-activity relationships (SAR) studies: a critical review. Bioorg Chem 2020; 105: 104400.

Farhan

Al-Jumaili

MHA

Bakr

EA.

New bis-heterocyclic structures: synthesis, characterization and biological activity. J Chem Res 2023; 47(6): 17475198231218387.

Kraja čić

Novak

Cindrić

, et al. Azithromycin–sulfonamide conjugates as inhibitors of resistant Streptococcus pyogenes strains. Eur J Med Chem 2007; 42(2): 138–145.

10.

Hillebrand

Liang

Serafim

, et al. Emerging and re-emerging warheads for targeted covalent inhibitors: an update. J Med Chem 2024; 67(10): 7668–7758.

11.

Ruankham

Pingaew

Prachayasittikul

, et al. Neuroprotective thiazole sulfonamides against 6-OHDA-induced Parkinsonian model: in vitro biological and in silico pharmacokinetic assessments. RSC Adv 2025; 15(6): 4281–4295.

12.

Liu

, et al. Synthesis, antibacterial activity, and action mechanism of novel sulfonamides containing oxyacetal and pyrimidine. J Agric Food Chem 2022; 70(30): 9305–9318.

13.

Ghorab

Soliman

El-Sayyad

, et al. Synthesis, antimicrobial, and antibiofilm activities of some novel 7-methoxyquinoline derivatives bearing sulfonamide moiety against urinary tract infection-causing pathogenic microbes. Int J Mol Sci 2023; 24(10): 8933.

14.

Agrawal

Patel

Synthesis, biological activity of newly designed sulfonamide based indole derivative as anti-microbial agent. Future J Pharm Sci 2023; 9(1): 17.

15.

Apaydın

Török

Sulfonamide derivatives as multi-target agents for complex diseases. Bioorg Med Chem Lett 2019; 29(16): 2042–2050.

16.

Gois

Lopes

Trindade

. 3.1.7. Preparation of a sulfathiazole prodrug via N-acylation with succinic anhydride. Compr Org Chem Exp Lab Classroom 2016: 151.

17.

El-Gaby

Ammar

El-Qaliei

MIH

, et al. Sulfonamides: synthesis and the recent applications in medicinal chemistry. Egypt J Chem 2020; 63(12): 5289–5327.

18.

Al-Jumaili

MHA

Ocak

Torun

Hydrogen-bonded ionic liquid crystals based on multi-armed structure: synthesis and characterization. Monatsh Chem 2022; 153(10): 939–947.

19.

Gaffer

Mahmoud

El-Sedik

, et al. Synthesis, molecular modelling, and antibacterial evaluation of new sulfonamide-dyes based pyrrole compounds. Sci Rep 2024; 14(1): 10973.

20.

Eaton

Symons

MCR

Rastogi

. Spectroscopic studies of the solvation of amides with N–H groups. Part 1.—The carbonyl group. J Chem Soc Faraday Trans 1 Phys Chem Condens Phases 1989; 85(10): 3257–3271.

21.

Threlfall

. The infrared spectra of amides. Part 1. The stretching vibrations of primary carboxamides. Vibr Spectrosc 2022; 121: 103386.

22.

Saifi

Ali

Inam

, et al. Synthesis and antibacterial evaluation of quinoline–sulfonamide hybrid compounds: a promising strategy against bacterial resistance. RSC Adv 2025; 15(3): 1680–1689.

Supplementary Material

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Synthesis,characterization,and biological activity of some novel sulfonamide derivatives

Abstract

Keywords

Introduction

Material and methods

Results and discussion

Biological activity

Experimental section

General procedure for synthesis of compound (1–3)

2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-(5-methylisoxazol-3-yl)benzo[d]thiazole-6-sulfonamide (1)

2-(1,3-dioxoisoindolin-2-yl)-N-(5-methylisoxazol-3-yl)benzo[d]thiazole-6-sulfonamide (2)

2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)-N-(5-methylisoxazol-3-yl)benzo[d]thiazole-6-sulfonamide (3)

General procedure for synthesis of compounds (5–7)

Synthesis 2-(chlorodiazenyl)-N-(5-methylisoxazol-3-yl)benzo[d]thiazole-6-sulfonamide (4a)

2-((2-chloro-5-formylphenyl)diazenyl)-N-(5-methylisoxazol-3-yl)benzo[d]thiazole-6-sulfonamide (5)

2-((5-formyl-2-hydroxyphenyl)diazenyl)-N-(5-methylisoxazol-3-yl)benzo[d]thiazole-6-sulfonamide (6)

((2-(dimethylamino)-5-formylphenyl)diazenyl)-N-(5-methylisoxazol-3-yl)benzo[d]thiazole-6-sulfonamide (7)

Conclusion

Supplemental Material

sj-docx-1-chl-10.1177_17475198251362960 – Supplemental material for Synthesis, characterization, and biological activity of some novel sulfonamide derivatives

Footnotes

Acknowledgements

ORCID iD

Consent to Participate

Consent for Publication

Funding

Declaration of Conflicting Interests

Data Availability Statement

Supplemental Material

References

Supplementary Material