Synthesis,spectral analysis and anti-cancer activity of N-((4H-1,2,3

Abstract

A thorough guide to the design and high-yield synthesis of 1,2,3-triazole derivatives using a variety of chemicals, bases, and catalysts is presented in this study. The approach is straightforward, effective, and efficient. Amide coupling reagents have been developed that are more convenient, milder, and allow for higher selectivity under mild conditions. 4-benzyl aniline (I) treated with propargyl bromide and K₂CO₃, DMF to form compound (II), compound (II) reacts with alkyl azide(III) and CuI / DHQ D₂. The derivatives of IV a-l have been shown moderate to excellent efficacy when tested for anticancer properties against several cancer cell lines. The MCF-7 cell line is the most resistant to compounds IV a and IV e, with an IC₅₀ values of 1.72 and 1.54 respectively. The structures of the newly synthesised compounds have been established by ¹H and ¹³C NMR, IR and ESI-HRMS.

Keywords

triazole benzyl aniline anticancer activity

Introduction

Three nitrogen atoms and two carbon atoms with two double bonds make up the unsaturated, aromatic, five-membered, $π$ - excessive nitrogen heterocycle known as 1,2,3-triazole, which has a 6π electron ring structure. The aromatic nature of 1,2,3-triazole is caused by sp2 hybridization and the delocalization of accessible 6π electrons around the ring.

In medicinal chemistry 1,2,3 triazoles are crucial because they can be utilized to create a wide range of heterocyclic compounds with various biological functions, including Antimicrobial,^1–4 Anti HIV,⁵ Anti bactrial,^5–7 Anticancer,^8–11 Antimalerial.¹² In addition, they have been employed as corrosion inhibitions, light stabilizers, optical brighteners, and herbicides. Strong anti bacterical, cytostatic and anti-inflammatory properties have been shown^13–17 for 1,2,3-triazole derivatives. 1,2,3 triazole moieties improve the solubility and hydrogen bonding of biomolecular drugs to the target and are resistant to metabolic degradation, they are ideal connecting units.¹⁸

In keeping with our interest in the synthesis of novel chemicals, the current work aims to try to synthesize molecules that comprise both the triazole and benzyl aniline systems. In order to do this, we offer here a simple, quick, and effective method for creating physiologically active 1,2,3 triazole derivatives using a range of chemicals. In addition, a series of novel derivatives. In addition, a series of novel derivatives IV a-j of hybrid molecules were synthesized, and the anticancer activity of these molecules was examined.

Results and discussion

Novel 1,2,3 triazole derivatives were efficiently synthesized in excellent yield by the popular ‘click chemistry.’^19–21 4-benzyl aniline was reacted with propargyl bromide of K₂CO₃, DMF will give compound (II), Compound II was reacted with appropriate azide in the presence of CuI as catalyst and DHQD₂(PHAL) as ligand in H₂O/ DMF for 1–2hrs scaffolding 1,4-disubstituted 12,3-triazoles in good excellent yield. (scheme 1). The structure of the synthesised compound was conformed by ¹H and ¹³C NMR spectroscopy. The 1H NMR spectrum showed a singlet at δ 8.15 ppm corresponding to Triazole proton, while aromatic proton appeared in the region δ 7.10–7.80 ppm. The NH2 proton of the aniline moiety were observed as a board signal around δ 6.20 ppm. In the ¹³C NMR spectrum, signals between δ 120–145 ppm were assigned to aromatic and Triazole carbons.

Scheme 1.

Synthetic pathway to derivatives of triazole IV a-l.

In vitro anti cancer activity

The compound IV a-l were tested for their anticancer properties by measuring their ability to supress the proliferation of tumour cell lines in 96 well mediated reduction of tetrazolium salt to water-insoluble crystal formation, with doxorubicin used as the reference. Cytotoxicity against a panel of four human tumor cell lines was assessed using the MTT tests: HEK 293 (normal human embryonic kidney cell line), MDA-MB 231 (derived from human breast adenocarcinoma cell), Hela (derived from human cervical cancer cells), and A549 (derived from alveolar adenocarcinoma epithelial cells). Graphing absorbance data for dosage response curve allowed for the determination of inhibitory concentration IC₅₀ values. The average standard deviation of three different experiments is used to display the IC₅₀ values in µM. The bulk of the generated compounds showed a significant cytotoxic effect on every cell line examined, as a Table 1 demonstrates, with multiple compounds exhibiting protencies comparable to the industry standard doxorubicin. With IC₅₀ values of 1.72 and 1.54 µM, IVa and IVe shown the strongest action against the MCF-7 cell line among the compounds under study. In contrast, IVb, IVd, IVg, IVh, IVj, IVk, and IVl had encouraging activity against the MDA-MB-231 and Hela cell lines.

Table 1.

In vitro anti cancer activity of compounds.

	IC₅₀ values in µM				HEK 293
Compound	A 549	Hela	MDAMB 231	MCF7	>100
Iva	6.05	3.42	4.12	1.72	>100
Ivb	7.01	3.78	4.14	8.21	>100
Ivc	>100	3.66	4.89	>100	>100
Ivd	10.04	3.72	5.62	6.24	>100
Ive	11.09	3.88	6.45	1.54	>100
Ivf	>100	5.14	4.08	>100	>100
Ivg	6.02	3.72	4.11	7.81	>100
Ivh	12.05	2.75	4.01	10.21	>100
Ivi	>100	3.76	3.74	>100	>100
Ivj	7.09	2.65	3.43	9.21	>100
Ivk	6.01	2.59	3.10	8.45	>100
Ivl	7.06	2.46	2.10	6.67	>100
Doxorubicin	0.461	0.609	0.71	1.25	>100

Experimental section

We used electrothermal 9002 melting point equipment to get an exact result. Infrared spectra can also be recorded by the FTS-6000 BIO RAD apparatus. ¹H and ¹³C NMR spectra were recorded using a bruker AC 300 in DMSO. Both coupling constant (J) and chemical shift (ppm) were expressed in hertz (HZ). For mass spectroscopy (HRES MS), we employed micromass LCT (electrospray ionization, positive mode) spectrometers. All reactions on aluminium sheets of sds silica gel 60 f 254 0.2 mm 4- dimethyl amino pyridinium were tracked using TLC.

Spectral data of synthesized compounds

4-benzyl- N-((1phenyl-1H-1,2,3-triazole-4-yl)methyl)aniline, Via: Yield 68%. m.p 189–190° C. IR (KBr) : 3314–3420 cm⁻¹ 400 MHz ¹H NMR (DMSO): δ ppm: 3.90 (s,2H, CH₂), 4.38 (s,2H, CH₂), 7.20–7.30 (m,5H Ar-H), 7.00–7.09 (m, 4H, Ar-H) 6.28 (s, 1H, NH) 7.40 7.75 (m,5H, Ar-H) 8.08 (s,1H, CH); ¹³C NMR (DMSO) : δ 146.8, 141.5, 136.8, 132.8, 130.5, 129.2, 128.7, 128.2, 128.0, 126.2, 120.5, 119.1, 114.0, 42.3, 41.3 ; MS: (M + H) : m/z 340.17. Found 340.43.Anal. Cacld for C₂₂H₂₀N₄ : C, 77.62; H, 5.92; N, 16.46. Found: C, 77.73; H, 6.10; N, 16.53.

4-(4-(((4-benzylphenyl)amino)methyl)-1-H-1,2,3 triazol-1-yl)phenol, via: 69%. M.p 190–191⁰C. IR (KBr): 3250–3450 cm⁻¹ 400 MHz ¹H NMR (DMSO) : δ ppm: 3.97 (s,2H,CH₂), 4.37 (s,2H CH₂), 6.55–6.90(m,4H, Ar H), 7.20–7.35(m, 5H, Ar H), 7.40–7.78(m,4H Ar-H),8.32 (s,1H CH), 6.28 (s,1H,NH), 10.19 (s,1H OH); ¹³C NMR (DMSO): δ 158.5, 146.8, 141.5, 132.8, 130.5129.4, 129.2, 129.4, 128.2, 126.2, 122.7, 120.4, 119.1, 115.9, 114.0, 42.3,41.3; MS: (M + H) : m/z 356.16. Found 356.43. Anal. Cald for C₂₂H₂₀N₄O : C, 74.14; H,5.66; N, 15.72; O, 4.49; Found: C, 74.20; H, 5.78; N, 16.01; O, 4.73.

4-benzyl-N-((1-(4-nitrophenyl-1H-1,2,3-triazol-4-yl)methyl)aniline, via 70%. M.p 190–200° C. IR (KBr): 3200–3350 cm⁻¹ 400 MHz ¹H NMR (DMSO) : δ ppm : 3.97 (s, 2H,CH₂), 4.39 (s, 2H CH₂), 6.28 (s,1H NH), 6.90–7.15 (m,4 H Ar- H), 7.20–7.35 (m, 5H Ar-H), 8.32 (t, CH), 8.11–8.49 (m 4 H-Ar H); ¹³C NMR (DMSO)δ : 147.9, 146.8,142.9, 141.5, 129.2, 126.2, 128.2, 120.9,1204, 119.1, 114.0, 41.2, 40.1 ; MS: (M + H) 385.15. Found 385.43. Anal. Cald for C₂₂H₁₉N₅O₂ : C, 68.56; H, 4.97; N, 18.17; O, 8.30 Found C, 62.67; H, 5.01; N, 18.22; O, 8.36.

4-benzyl-N-((1-(4-chlorophenyl-1H-1,2,3-triazol-4-yl)methyl)aniline via: 70% m.p 170–180⁰C . IR (KBr): 3250–3340 cm⁻¹ 400 MHz ¹H NMR (DMSO) : δ ppm : 3.97 (s, 2H, CH₂), 4.30 (s,2H,CH₂), 6.26 (s, 1H, NH), 6.95–7.20 (m, 5 H Ar-H), 7.20–7.40 (m, 4H, Ar-H), 7.45–7.90 (m 4H, Ar-H), 8.30 (t,CH) ; ¹³C NMR (DMSO) δ : 146.8, 141.5, 134.9, 134.3, 132.8, 130.5, 129.2, 128.2, 126.2, 122.0, 120.4, 119.1, 114.0, 42.3, 41.1; MS: (M + H) 374.13. Found : 374.87. Anal. cald for C₂₂H₁₉Cl N₄ : C, 70.49; H, 5.11; Cl, 9.46; N, 14.95 Found : C, 70.53; H, 5.21; Cl, 9.59; N, 15.12

4-benzyl –N- ((1-(4- Bromophenyl-1H-1,2,3 triazol-4-yl)methyl)aniline Via : 71% m.p 180–190⁰C . IR (KBr) : 3260–3359 cm⁻¹ 400 MHz ¹H NMR (DMSO) δ ppm : 3.92 (s,2H, CH₂), 4.35 (s, 1H CH₂), 6.28 (s, 1H, NH), 6.98- 7.20 (m, 5H Ar-H), 7.23–7.50 (m 4H, Ar-H) 7.60–7.90 (m 4 H Ar-H), 8.29 (t-CH), ¹³C NMR (DMS0) δ : 146.3, 141.7, 134.3, 132.7, 130.5, 129.2, 128.2, 126.2, 123.1, 122.0, 120.4, 119.5, 114.3.42.6, 41.5; MS(M + H) : 418.08. Found : 419.33. Anal cald for C₂₂H₁₉BrN₄ : C, 63.08; H,4.57; Br, 19.06; N, 13.36; Found : C, 63.22; H, 4.64; Br, 19.12; N, 13.42

4-benzyl-N-((1-(4-fluorophenyl)-1H-1,2,3triazol-4-yl)methyl)aniline Via: 72% m.p 190–198⁰C IR (KBr) : 3300–3350 cm⁻¹ 400 MHz ¹H NMR (DMSO) δ ppm : 3.95 (s, 2H, CH₂), 4.58 (s,2H CH₂), 6.26 (s, 1H NH), 6.55–6.90 (m, 5H Ar-H), 7.12–7.50 (m,4H Ar-H),7.60–7.99 (m 4H Ar-H), 8.23 (t CH); ¹³C NMR (DMSO) δ :162.9, 146.8, 141.5,132.8, 130.5,129.4, 128.2, 126.2, 122.5, 119.1, 115.3, 114.0, 43.2, 41.2 ; MS (M + H) 358.16. Found : 358.42. Anal cald for : C₂₂H₁₉FN₄ : C, 73.72; H, 5.34; F, 5.30; N, 15.63; Found : C,73.91; H, 5.39; F, 5.65; N, 15.80

4- benzyl-N-((1-(4-iodophenyl)-1H-1,2,3triazol-4-yl)methyl)aniline Via : 73% m.p 193–199⁰C. IR (KBr) : 3250–3400cm⁻¹ 400 MHz ¹ HNMR (DMSO) δ : 3.92 (s, 2H,CH₂), 4.52 (s,2H CH₂), 6.24 (s, 1 H NH), 7.13 (m, 5H, Ar-H), 7.30 (d, J = 7.1 Hz, 2H, Ar-H), 7.50 (m, 2H, Ar-H),7.60–7.90 (m 4H Ar-H), 8.32 (t, CH); ¹³ C NMR (DMSO) δ : 146.8, 141.5, 137.6, 135.6,132.8, 131.2, 130.5, 129.2, 126.2, 120.4, 119.1, 114.0, 94.3, 42.3, 41.3 ; MS (M + H); 466.07. Found: 466.33. Anal cald for : C₂₂H₁₉IN₄ : C, 56.66; H,4.11; I,27.21; N,12.06 ; Found :C, 56.82; H, 4.21; I, 27.32; N, 12.12.

4-(4-(((4- benzylphenyl)amino)methyl)-1H-1,2,3-triazol-1-yl)benzonitrile Via 74%. m.p 180–190⁰C IR (KBr) : 2240- 2260 cm⁻¹ 400 MHz ¹H NMR (DMSO) δ : 3.95 (s, 2H, CH₂), 4.51 (s,2H, CH₂), 6.26 (1H, NH), 7.10 (m, 5 H Ar-H), 7.30 (d, J = 7.4 Hz,2H, Ar-H), 7.50(m, 2H, Ar-H), 7.80 (m 4H Ar-H), 8.35 (t CH); ¹³ C NMR (DMSO) δ ppm:146.8, 141.5, 137.6, 135.7, 133.3, 132.8, 131.2, 130.5, 129.2, 128.2, 126.5, 123.4, 120.6, 119.1, 114.0, 118.6, 12.6,42.3, 41.5 ; MS (M + H) ; 365.16. Found : 365.44. Anal cond for; C₂₃H₁₉N₅ : C, 75.59 ; H, 5.24 ; N, 19.16 ;Found : C, 75.62; H, 5.30 ; N, 19.22.

4-benzyl-N-((1-(p-tolyl)-1H-1,2,3triazol-4-yl)methyl)aniline Via : 75%. M.p 170–180⁰C. IR (KBr) : 3000–3100 cm⁻¹ 400 MHz (DMSO) δ ppm : 3.78 (s,3H, CH₃), 3.90 (s, 2H, CH₂), 4.45 (s, 2H, CH₂), 6.25 (s,1H NH), 7.10 (m, 5HAr-H), 7.350 (d,J = 7.5 Hz,2H, Ar-H), 7.450 (m, 2H, Ar-H), 7.70 (m 4H, Ar-H), 8.28 (s, 1H, CH); ¹³C NMR (DMSO) δ ppm: 146.5, 141.5, 138.4, 134.8, 133.8, 132.8,130.5, 129.0, 128.2, 126.2, 120.4, 119.1, 114.0, 42..5, 41.3, 22.3 ; MS (M + H) : 354.18. Found : 354.46. Anal cond for: C₂₃H₂₂N₄ : C, 77.94; H,6.26; N, 15.91; Found : C, 78.01; H, 6.35, N, 15.97.

4-benzyl-N-((1-(4-difluoromethoxy)phenyl)-1-H-1,2,3-triazol-4-yl) methyl)aniline Via 76%. M.p 185- 195⁰C. IR (KBr) : 3350–3420 cm⁻¹ 400 MHz (DMSO) δ : 3.97 (s, 2H, CH₂), 4.39 (s, 2H CH₂), 6.28 (s, 1H NH), 7.20 (m, 5H, Ar-H), 7.35 (d, J = 7.8 Hz, Ar-H), 7.55 (m, 2H, Ar-H), 7.36 (s, 1H, CH), 7.78 (m,4H, Ar-H), 8.32 (s, 1H, CH) ; ¹³C NMR (DMSO) δ ppm : 167.3, 160.6, 146.8,141.5, 132.8, 130.5, 129.2, 128.2, 126.2, 122.3, 120.4, 119.1, 114.3, 114.0, 42.3, 41.3 ; MS (M + H); 406.16. Found; 406.44. Anal cald for : C₂₃H₂₀F₂N₄O : C, 67.97; H, 4.96; F, 9.35; N,13.79; O, 3.94; Found : 68.02; H,5.00; F, 9.42; N,13.89; O,4.05.

4-benzyl-N-((1-ethylphenyl)-1H-1,2,3-triazol-4-yl)methyl)aniline Via : 77%. M.p. 187–195⁰C. IR (KBr) : 3050–3150 cm⁻¹ 400 MHz (DMSO) δ 1.98 (s,3H, CH₃), 2.98 (s, 2H, CH₂), 3.95 (s, 2H, CH₂), 4.35 (s, 2H, CH₂), 6.20 (s, 1H,NH), 7.30 (m, 5H, Ar-H), 7.60 (d. J = 7.2 Hz, Ar-2H), 7.36 (s, 2H, Ar-H), 7.65 (m, 4H, Ar-H), 8.31 (s,1H, CH) ; 13C NMR : 146.8, 144.3,141.8, 134.8, 134.0, 132.8, 130.5, 129.2, 128.2, 127.7, 126.2, 120.4, 119.1, 114.5, 43.3, 42.3, 28.4, 14.9 ; MS (M + H) ; 367.20, Found : 367.50. Anal cald for : C₂₅H₂₅N₃ : C, 81.71; H,6.86, N,11.43; Found : C, 81.81; H, 6.89 ; N, 11.56.

4-benzyl-N-((1- methoxyphenyl)-1H-1,2,3-triazol-4-yl)methyl)aniline Via : 78%. M.p 189–198⁰C. IR (KBr) : 330–3100cm⁻¹ 400 MHz (DMSO) δ : 3.97 (s, 2H, CH₂), 4.39 (s, 2H CH₂), 4.04 (s, 3H CH₃), 6.22 (s,1H NH), 7.22 (m, 5H Ar-H), 7.43 (d, J = 7.4 Hz, Ar- 2H), 7.57.89 (m, 4 H, Ar-H), 2 (S, 2H, Ar-H), 8.28 (s, 1H CH) ; ¹³C NMR : 160.6, 146.4, 141.5, 132.5, 130.5,129.2, 128.1, 126.2, 122.3, 120.4, 119.1, 114.3, 55.8, 42.3, 41.3 ; MS (M + H) : 294.15. Found : 294.36. Anal cald : for: C₂₃H₂₂N₄O : C, 74.57; H,5.99; N, 15.13; O, 4.32 ; Found : C, 74.69; H, 6.14 ; N,15.19; O,4.42.

Conclusion

The new 12,3 triazole were synthesised. All developed organic compounds exhibited strong characteristics. biological properties of 12,3 triazole cmpounds are more significant. The complexes anti cancer activity was analyzed. The MCF-7 cell line was most sensitive to compounds 1a and 1e, with IC50values of 1.72 and 1.54 M, respectively. Promising action against MDA- MB-231 and Hela cell lines was shown with compounds IV k and IV l.

Supplemental Material

sj-docx-1-mgc-10.1177_10241221261447775 - Supplemental material for Synthesis, spectral analysis and anti-cancer activity of N-((4H-1,2,3 – triazole-4-yl)methyl-4-benzylaniline

Supplemental material, sj-docx-1-mgc-10.1177_10241221261447775 for Synthesis, spectral analysis and anti-cancer activity of N-((4H-1,2,3 – triazole-4-yl)methyl-4-benzylaniline by G. Manasa and Ch. Sunitha in Main Group Chemistry

Footnotes

Acknowledgment

The authors extend their gratitude to the Director of the Indian Institute of Chemical Technology, Hyderabad. Additionally, the department of chemistry at Vaagdevi Degree and P.G college, Hanamkonda. Furthermore, the director of the centre for cellular and molecular Biology in Hyderabad is also accountable for providing biological activity and spectrum data.

ORCID iD

G. Manasa

Funding

The authors received no financial support for the research, authorship, and/or publication of this article.

Declaration of conflicting interests

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

Supplemental material

Supplemental material for this article is available online.

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Synthesis,spectral analysis and anti-cancer activity of N-((4H-1,2,3 – triazole-4-yl)methyl-4-benzylaniline