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ORIGINAL ARTICLE
Year : 2009  |  Volume : 1  |  Issue : 1  |  Page : 27-31 Table of Contents     

Synthesis and antimicrobial activity of 2-chloro-6-methylquinoline hydrazone derivatives


Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard (Hamdard University), New Delhi - 110 062, India

Date of Submission14-Nov-2009
Date of Decision27-Nov-2009
Date of Acceptance04-Dec-2009
Date of Web Publication23-Apr-2010

Correspondence Address:
Suresh Kumar
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard (Hamdard University), New Delhi - 110 062
India
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Source of Support: None, Conflict of Interest: None


DOI: 10.4103/0975-7406.62683

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   Abstract 

Purpose : A series of 2-chloro-6-methylquinoline hydrazones (3a-o) were synthesized by the condensation of substituted acyl hydrazines, semicarbazide, thiosemicarbazide, and INH with 2-chloro-3-formyl-6-methylquinoline in absolute alcohol and were tested for antimicrobial activity. Materials and Methods : The structures of compounds were established using modern analytical technique FT-IR, 1 H and 13 C-NMR, mass spectral data and elemental analysis. All the compounds were evaluated for their antibacterial activity against Escherichia coli (NCTC 10418), Staphylococcus aureus (NCTC 65710), and Pseudomonas aeruginosa (NCTC 10662). The compounds were also tested for antifungal activity aganist Aspergillus niger (MTCC 281), Aspergillus flavus (MTCC 277), Monascus purpureus (MTCC 369) and Penicillium citrinum (NCIM 768) by the cup-plate method. Results : It was observed that maximum antibacterial activity was shown by compounds having the 4-fluoro, 4-chloro, 4-nitro, and 2, 4-dicloro group in the benzoyl ring. Compounds were weakly active against fungal strains. Conclusion : Quinolinyl hydrazone of INH 3o was found to be most active toward the bacterial strains compared to their corresponding benzoyl derivatives.

Keywords: Antibacterial, antifungal activity, 2-chloro-3-formyl-6-methylquinoline, hydrazones


How to cite this article:
Bawa S, Kumar S, Drabu S, Kumar R. Synthesis and antimicrobial activity of 2-chloro-6-methylquinoline hydrazone derivatives. J Pharm Bioall Sci 2009;1:27-31

How to cite this URL:
Bawa S, Kumar S, Drabu S, Kumar R. Synthesis and antimicrobial activity of 2-chloro-6-methylquinoline hydrazone derivatives. J Pharm Bioall Sci [serial online] 2009 [cited 2019 Dec 9];1:27-31. Available from: http://www.jpbsonline.org/text.asp?2009/1/1/27/62683

Quinoline and its derivatives have been known to possess diverse pharmacological activities, such as, antibacterial, antifungal, antimycobacterial, antidepressant, antimalarial, anticonvulsant, antiviral, anticancer, hypotensive, and anti-inflammatory activities. [1],[2],[3],[4],[5],[6],[7],[8],[9],[10] Due to their interesting physiological properties, quinoline derivatives in particular are extremely important and are frequently found in privileged structures (pharmacophore), in numerous biologically active compounds. [11] Moreover, hydrazones of various heteroaryl rings have shown important antibacterial activity. [12],[13],[14],[15],[16] In the present investigation it was thought worthwhile to combine two potential pharmacophores in a single matrix and to evaluate them for their synergistic antimicrobial activity.


   Materials and Methods Top


The melting points were determined by the open capillary method, using the electrical melting point apparatus, and were uncorrected. The IR spectra were recorded as KBr (pallet) on the Bio Rad FT-IR spectrophotometer. 1 H and 13 C-NMR spectra were recorded on the Bruker DPX 300 MHz spectrophotometer using Tetramethylsilane (TMS) as the internal standard. The mass spectra were recorded on JEOL SX102/DA-6000 mass spectrometer and the elemental analysis was carried out on Vario-EL III CHNOS - Elemantar analyzer.

The lipophilicity of the compounds was calculated by using the Chemsketch 12.0 software of the Advanced Chemistry Development, Inc. (ACD) laboratory. Thin Layer Chromatography (TLC) was performed to check the purity of the compounds, the spot being located under iodine vapors.

Synthesis of 2-chloro-3-formyl-6-methylquinoline 2

N,N- Dimethylformamide (0.125 mol) was cooled to 0˚C in a flask equipped with a drying tube, and phosphoryl chloride (0.35 mol) was added drop wise, with stirring. To this solution was added p-methylacetanilde 1 (0.05 mol) and after five minutes the solution was heated under reflux for 16.5 hours at 75˚C. The reaction mixture was cooled and poured into ice water (300 mL) and stirred for 30 minutes at 0 - 10˚C. The precipitate formed was filtered off and washed with cold water, dried, and recrystallized from ethyl acetate as light yellow, shiny, needle-shaped crystals of 2-chloro-3-formyl-6-methylquinoline. [17]

Yield; 61 %, m.p. 140-141. IR (KBr) cm -1 : 1698 (C=O), 1610 (C=C), 1595 (C=N), 751 (C-Cl). 1 H-NMR (300 MHz, DMSO-d 6 ) δ: 2.52 (s, 3H, CH 3 ), 7.54-7.56 (m, 2H, H-5 and H-7), 7.90-7.93 (d, 1H, H-8, J = 7.72 Hz), 8.63 (s, 1H, H-4). 10.52 (s, 1H, CHO). 13 C-NMR (75 MHz, DMSO-d 6) δ: 19.03 (CH 3 ), 125.89, 126.36, 127.52, 132.91, 136.12, 141.21, 148.18, 187.97 (CHO). FAB-MS m/z: 206 (M + ), 208 (M+2).

The various substituted acyl hydrazines were synthesized as per the method reported in the literature. [18]

Synthesis of compounds 3a-o

To a solution of compound 2 (0.005 mol) in 20 ml of absolute ethanol, an equimolar amount of substituted acyl hydrazines / semicarbazide / thiosemicarbazide (0.005 mol) was added and the mixture was refluxed for four to six hours. On cooling, a solid was obtained that was filtered, washed with hot methanol, dried, and recrystallized from an ethanol:DMF mixture, to give the final compounds.

N'-[(2-chloro-6-methylquinolin-3-yl) methylidene] benzohydrazide 3a

IR (KBr) cm -1 : 3261 (N-H), 1655 (C=O), 1627 (C=N), 1589 (C=C), 759 (C-Cl). 1 H-NMR (300 MHz, DMSO-d 6): δ 2.51 (s, 3H, CH 3 ), 7.57-7.64 (m, 3H, H-3', 4' and 5'), 7.70-7.73 (d, 1H, H-7, J = 8.49 Hz), 7.85-7.88 (d, 1H, H-8, J = 8.52 Hz), 7.97-8.01 (m, 3H, H-2', 6'and 5), 8.82 (s, 1H, H-4), 8.93 (s, 1H, CH=N), 12.26 (s, 1H, CONH). 13 C-NMR (75 MHz, DMSO-d 6); δ 19.89, 121.85, 126.58, 127.37, 128.24, 128.93, 131.63, 132.08, 136.31, 141.88, 146.69, 149.37, 156.81 (C=N), 169.08 (C=O). FAB-MS m/z: 324 (M + ), 326 (M+2). [Figure 1]

N'-[(2-chloro-6-methylquinolin-3-yl)methylidene]-4-methylbenzohydrazide 3b

IR (KBr) cm -1 : 3223 (N-H), 1668 (C=O), 1622 (C=N), 1597 (C=C), 751 (C-Cl). 1 H-NMR (300 MHz, DMSO-d 6): δ 2.40 (s, 3H, CH 3 ), 2.52 (s, 3H, CH 3 ), 7.35-7.38 (d, 2H, H-3' and 5', J = 7.68 Hz), 7.69-7.72 (d, 1H, H-7, J = 8.43 Hz), 7.87-7.89 (d, 3H, H- 2', 6' and 8, J = 8.07 Hz), 7.98 (s, 1H, H-5), 8.84 (s, 1H, H-4), 8.91 (s, 1H, CH=N), 12.19 (s, 1H, CONH). 13 C-NMR (75 MHz, DMSO-d 6); δ 18.93 (CH 3 ), 21.17 (CH 3 ), 120.80, 126.07, 127.90, 128.14, 129.10, 130.93, 133.21, 136.08, 142.87, 147.54, 149.07, 159.01, 167.89 (C=O). FAB -MS : m/z 338 (M) + , 340 (M+2),

N'-[(2-chloro-6-methylquinolin-3-yl)methylidene]-4-methoxybenzohydrazide 3c

IR (KBr) cm -1 : 3223 (N-H), 1673 (C=O), 1629 (C=N), 1588 (C=C), 761 (C-Cl). 1 H-NMR (300 MHz, DMSO-d 6); δ 2.49 (s, 3H, CH 3 ), 3.82 (s, 3H, OCH 3 ), 7.31-7.34 (d, 2H, H-3' and 5', J = 7.72 Hz), 7.69-7.72 (d, 1H, H-7, J = 8.51 Hz), 7.85-7.88 (d, 1H, H-8, J = 8.42 Hz), 7.97-8.02 (m, 3H, H-2', 6' and 5), 8.83 (s, 1H, H-4), 8.92 (s, 1H, CH=N), 12.17 (s, 1H, CONH).

4-Chloro-N'-[(2-chloro-6-methylquinolin-3-yl) methylidene] benzohydrazide 3d

IR (KBr) cm -1 : 3264 (N-H), 1683 (C=O), 1630 (C=N), 1589 (C=C), 757 (C-Cl). 1 H-NMR (300 MHz, DMSO-d 6): δ 2.51 (s, 3H, CH 3 ), 7.63-7.65 (d, 2H, H-3' and 5' J = 8.38 Hz), 7.69-7.72 (d, 1H, H-7, J = 8.56 Hz), 7.86-7.89 (d, 1H, H-8, J = 8.59 Hz), 7.98-8.01 (m, 3H, H-2', 6' and 5), 8.85 (s, 1H, H-4), 8.91 (s, 1H, CH=N), 12.25 (s, 1H, CONH) [Table 1].

2,4-Dichloro-N'-[(2-chloro-6-methylquinolin-3-yl)methylidene]benzo hydrazide 3e

IR (KBr) cm -1 : 3220 (N-H), 1672 (C=O), 1629 (C=N), 1582 (C=C), 763 (C-Cl). 1 H-NMR (300 MHz, DMSO-d 6); δ 2.52 (s, 3H, CH 3 ), 7.66-7.73 (m, 3H-3' and 5' , 7), 7.86-7.89 (m, 2H, H- 6' and 8), 7.97 (s, 1H, H-5), 8.83 (s, 1H, H-4), 8.94 (s, 1H, CH=N), 12.19 (s, 1H, CONH).

4-Bromo-N'-[(2-chloro-6-methylquinolin-3-yl) methylidene] benzohydrazide 3f

IR (KBr) cm -1 : 3264 (N-H), 1675 (C=O), 1630 (C=N), 1579 (C=C), 753 (C-Cl). 1 H-NMR (300 MHz, DMSO-d 6): δ 2.52 (s, 3H, CH 3 ), 7.60-7.63 (d, 2H, H-3'and 5' J = 8.32 Hz), 7.70-7.73 (d, 1H, H-7, J = 8.54 Hz), 7.86-7.89 (d, 1H, H-8, J = 8.62 Hz), 7.97-8.01 (m, 3H, H-2', 6' and 5), 8.86 (s, 1H, H-4), 8.94 (s, 1H, CH=N), 12.21 (s, 1H, CONH).

N'-[(2-chloro-6-methylquinolin-3-yl)methylidene]-4-fluorobenzohydrazide 3g

IR (KBr) cm -1 : 3254 (N-H), 1673 (C=O), 1630 (C=N), 1576 (C=C), 756 (C-Cl). 1 H-NMR (300 MHz, DMSO-d 6); δ 2.48 (s, 3H, CH 3 ), 7.64-7.66 (d, 2H, H-3' and 5' J = 8.15 Hz), 7.69-7.72 (d, 1H, H-7, J = 8.37 Hz), 7.85-7.88 (d, 1H, H-8, J = 8.45 Hz), 7.97-8.00 (m, 3H, H-2', 6' and 5), 8.87 (s, 1H, H-4), 8.96 (s, 1H, CH=N), 12.19 (s, 1H, CONH).

N'-[(2-chloro-6-methylquinolin-3-yl)methylidene]-4-nitrobenohydrazide 3h

IR (KBr) cm -1 : 3237 (N-H), 1696 (C=O), 1632 (C=N), 1586 (C=C), 759 (C-Cl). 1 H-NMR (300 MHz, DMSO-d 6); δ 2.52 (s, 3H, CH 3 ), 7.57-7.60, (d, H-3' and 5', J = 7.68 Hz), 7.69-7.72 (d, 1H, H-7, J = 8.43 Hz), 7.87-7.89 (d, 3H, H- 2', 6' and 8 J = 8.07 Hz), 7.98 (s, 1H, H-5), 8.84 (s, 1H, H-4), 8.91 (s, 1H, CH=N), 12.19 (s, 1H, CONH).

N'-[(2-chloro-6-methylquinolin-3-yl)methylidene]-3-methylbenzohydrazide 3i

IR (KBr) cm -1 : 3261 (N-H), 1661 (C=O), 1627 (C=N), 1589 (C=C), 765 (C-Cl). 1 H-NMR (300 MHz, DMSO-d 6); δ 2.41 (s, 3H, CH 3 ), 2.52 (s, 3H, CH 3 ), 7.37-7.42 (m, 2H, H-4' and 5'), 7.69-7.72 (d, 1H, H-7, J = 8.33 Hz), 7.86-7.91 (m, 3H, H-2', 6' and 8), 8.0 (s, 1H, H-5), 8.81 (s, 1H, H-4), 8.93 (s, 1H, CH=N), 12.20 (s, 1H, CONH).

N'-[(2-chloro-6-methylquinolin-3-yl)methylidene]-2-phenylacetohydrazide 3j

IR (KBr) cm -1 : 3254 (N-H), 1668 (C=O), 1636 (C=N), 1580 (C=C), 768 (C-Cl). 1 H-NMR (300 MHz, DMSO-d 6); δ 2.48 (s, 3H, CH 3 ), 3.69 (s, 2H, CH 2 ), 7.34-7.47 (m, 5H, H-2',3', 4', 5', 6'), 7.70-7.73 (d, 1H, H-7, J = 8.16 Hz), 7.87-7.90 (m, 2H, H- 5 and 8), 8.84 (s, 1H, H-4), 8.96 (s, 1H, CH=N), 12.17 (s, 1H, CONH).

N'-[(2-chloro-6-methylquinolin-3-yl)methylidene]-2-(4-chlorophenyl)aceto hydrazide 3k

IR (KBr) cm -1 ; 3261 (N-H), 1655 (C=O), 1627 (C=N), 1589 (C=C), 758 (C-Cl). 1 H-NMR (300 MHz, DMSO-d 6): δ 2.50 (s, 3H, CH 3 ), 3.72 (s, 2H, CH 2 ), 7.43-7.46 (d, 2H, H-2' and 6', J = 8.17 Hz), 7.69-7.75 (m, 3H, H- 3', 5' and 7), 7.86-7.89 (d, 1H, H-8, J = 8.37), 7.97 (s, 1H, H-5), 8.82 (s, 1H, H-4), 8.94 (s, 1H, CH=N), 12.18 (s, 1H, CONH).

N'-[(2-chloro-6-methylquinolin-3-yl)methylidene]-2-phenoxyacetohydrazide 3l

IR (KBr) cm -1 : 3220 (N-H), 1670 (C=O), 1631 (C=N), 1584 (C=C), 757 (C-Cl). 1 H-NMR (300 MHz, DMSO-d 6); δ 4.70 (s, 2H, OCH 2 ), 7.31-7.38 (m, 5H, H-2',3', 4', 5', 6'), 7.67-7.70 (d, 1H, H-7, J = 8.52 Hz), 7.86-7.89 (d, 1H, H-8, J = 8.36 Hz), 7.99 (s, 1H, H-5), 8.81 (s, 1H, H-4), 8.92 (s, 1H, CH=N), 12.17 (s, 1H, CONH).

2-[(2-chloro-6-methylquinolin-3-yl)methylidene] hydrazinecarboxamide 3m

IR (KBr) cm -1 : 3271 (N-H), 1677 (C=O), 1631 (C=N), 1589 (C=C), 763 (C-Cl). 1 H-NMR (300 MHz, DMSO-d 6): δ 2.53 (s, 3H, CH 3 ), 4.97 (s, 2H, NH 2 ), 7.68-7.71 (d, 1H, H-7, J = 8.46 Hz), 7.84-7.87 (d, 1H, H-8, J = 8.33 Hz), 7.98 (s, 1H, H-5), 8.80 (s, 1H, H-4), 9.11 (s, 1H, CH=N), 11.31 (s, 1H, CONH).

2-[(2-chloro-6-methylquinolin-3-yl)methylidene] hydrazinecarbothioamide 3n

IR (KBr) cm -1 : 3243 (N-H), 1358 (C=S), 1634 (C=N), 1569 (C=C), 756 (C-Cl). 1 H-NMR (300 MHz, DMSO-d 6): δ 2.51 (s, 3H, CH 3 ), 5.16 (bs, 2H, NH 2 ), 7.69-7.72 (d, 1H, H-7, J = 8.38 Hz), 7.83-7.86 (d, 1H, H-8, J = 8.20 Hz), 7.98 (s, 1H, H-5), 8.79 (s, 1H, H-4), 9.02 (s, 1H, CH=N), 11.29 (s, 1H, CONH).

N'-[(2-chloro-6-methylquinolin-3-yl)methylidene] pyridine-4-carbohydrazide 3o

IR (KBr) cm -1 : 3278 (N-H), 1679 (C=O), 1629 (C=N), 1588 (C=C), 756 (C-Cl). 1 H-NMR (300 MHz, DMSO-d 6): δ 2.51 (s, 3H, CH 3 ), 7.67-7.70 (d, 1H, H-7, J = 8.28 Hz), 7.83-7.87 (m, 3H, H-8 and 2 x pyridine), 7.99 (s, 1H, H-5), 8.77-8.80 (m, 3H, H-4 and 2 x pyridine), 9.02 (s, 1H, CH=N), 11.23 (s, 1H, CONH).

Antimicrobial activity

The newly synthesized compounds (3a-o) were tested against a panel of bacterial strains, namely,  Escherichia More Details coli (NCTC, 10418), Staphylococcus aureus (NCTC, 65710), and Pseudomonas aeruginosa (NCTC, 10662), and fungal strains, namely, Aspergillus niger (MTCC, 281), Aspergillus flavus (MTCC, 277), Monascus purpureus (MTCC, 369), and Penicillium citrinum (NCIM, 768) by using the cup-plate method. [19],[20] Potato dextrose agar (PDA) and nutrient agar were used as the culture mediums for the antifungal and antibacterial activity, respectively. Using an agar punch, wells were made on the seeded agar plates and a concentration of 200 μg/ml of the test compound in DMSO was added into each well, labeled previously. A control was also prepared using solvent DMSO. The petri plates were maintained at 30C for 72 hours for fungi, and 37C for 24 hours for bacteria. Antimicrobial activity was determined by measuring the zone of inhibition in millimeters and data have been presented as (n = 3, Mean S.D.) and compared with standard Fluconazole (200 μg/ml) and Ciprofloxacin (200 μg/ml), and the results have been summarized in [Table 2].


   Results and Discussion Top


The synthesis of compounds 3a-o was undertaken as per scheme 1. The required 2-chloro-3-formyl-6-methylquinoline 2 was prepared by the action of DMF / POCl 3 (Vilsmeier-Haack reaction) on p-methylacetanilinde 1. The various hydrazones, semicarbazones, and thiosemicarbazones 3a-o were synthesized by the condensation of 2-chloro-3-formyl-6-methylquinoline, with substituted acyl hydrazines, semicarbazide, thiosemicarbazide, and INH in absolute ethanol, in a yield ranging between 58 to 80%. All the compounds were characterized by IR and 1 H-NMR along with 13 C-NMR and FAB-MS spectra of some selected compounds. The elemental analysis data of compounds was found to be within 0.4% limit. The IR spectra of the final compounds (3a-o) showed absorption bands at 1655 - 1696 cm -1 appearing due to the presence of C=O functional group, while the band observed at 1596 - 1636 cm -1 corresponded with the C=N linkage. In the 1 H-NMR spectra the synthesis of the compounds (3a-o) was confirmed on the basis of the fact that the aldehydic proton, which was observed at d 10.52 in compound 2 disappeared, and a new signal was found arising due to the azomethine group CH=N, present in the final compounds (3a-o). The signal due to CH=N (azomethine), which was present in all the compounds was observed as a singlet varying from d values 8.79 - 9.11, integrating in one proton. The CONH proton resonated at d values between 11.23 and 12.26, as a singlet to a broad singlet, and this signal was absent when 1 H-NMR was recorded in the presence of D 2 O. The 6-CH 3 group of the quinoline was observed as a singlet integrating in three protons, resonating at d values ranging from 2.48 to 2.52, whereas, the H-5 and H-4 proton of the quinoline appeared as a singlet at values ranging from d 7.98 to 5.01 and 8.81 to 8.85, respectively. The H-5 proton was also observed as multiplets because of its overlapping with the benzoyl protons in compounds 3a, 3c, 3d, 3f, 3g, and 3j. The remaining two protons of the quinoline, that is, H-7 and H-8, split as doublets at δ values from 7.67 to 7.73 (J = 8.16 - 8.56 Hz) and 8.84 to 8.89 (J = 8.36 - 8.62 Hz), respectively.

In 13 C-NMR spectra of some of the selected compounds 3a and 3b, the carbon signal due to (-CHO) of intermediate 2, was observed at d values 187.97. However, this signal was found to be absent and a new signal at d values 156.81 and 159.01 arose due to the presence of CH=N in compound 3a and 3b, respectively, which further supported the synthesis of compounds (3a-o) in addition to the 1 H-NMR spectra. FAB-MS spectra of some selected compounds 3a and 3b registered a molecular ion (M + ) peak at m/z 324 and 338, along with the M + 2 peak at m/z 326 and 340, respectively.

Antimicrobial activity

The antibacterial results showed that some of the compounds were active against both Gram-positive and Gram-negative bacteria. Among the tested compounds (3a-o) compounds 3a, 3c, 3d, 3e, 3f, 3g, 3h, 3k, 3l, 3n, and 3o showed moderate-to- good antibacterial activity against the test organisms. It was observed that maximum antibacterial activity was shown by compounds having the 4-fluoro, 4-chloro, 4-nitro, and 2, 4-dicloro group in the benzoyl ring. The effect of spacers like CH 2 and CH 2 O between the benzoyl ring and the R-CH=NNHCO-R group of quinoline in compounds 3j, 3k, and 3l, on the antibacterial activity, was not prominent as indicated by no significant increase in the zone of inhibition. Furthermore, a compound with pyridine ring 3o was most active toward the bacterial strains compared to their corresponding benzoyl derivatives 3a. On the other hand semi-carbazone and thiosemicarbazone derivatives of quinoline were moderately active against bacteria strains. An antifungal screening data of the compounds revealed that among all the tested compounds, only some of the derivatives possessed antifungal activity at a concentration of 200 μg/ml, as shown by their zone of inhibition (< 10 mm). Moreover, these compounds were mostly active against the fungal strains Aspergillus niger (MTCC, 281) and Aspergillus flavus (MTCC, 277). The semi-carbazones and thiosemicarbazones derivatives were also weakly active against the fungal strains.


   Acknowledgments Top


The authors are thankful to the Department of Pharmaceutical Chemistry, the Faculty of the Pharmacy, Jamia Hamdard, for providing the necessary facility, and CDRI, Lucknow, India for recording the FAB-MS spectral data.

 
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19.Barry AL. The antimicrobial susceptibility test: Principle and Practice. Philadelphia: Illus Lea and Febiger; 1976. p. 180, Biol Abstr, 64, 1977, 25183.  Back to cited text no. 19      
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    Figures

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  [Table 1], [Table 2]


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