International Scholarly Research Notices

Research Article

Synthesis and Biological Evaluation of Some Novel 5-[(3-Aralkyl Amido/Imidoalkyl) Phenyl]-1,2,4-Triazolo[3,4-b]-1,3,4-Thiadiazines as Antiviral Agents

Table 1

Characterization data of m-(aralkyl amido/imidoalkyl) benzoic acids 1, m-(aralkyl amido/imidoalkyl) benzoic acid hydrazides 3, 4-amino-5-mercapto-3-[(3^′-aralkyl amido/imidoalkyl) phenyl]-1,2,4-triazoles 5, and 5-[(3^′-aralkyl amido/imidoalkyl) phenyl]-1,2,4-triazolo-[3,4-b]1,3,4-thiadiazines 6.


Compound	R	R¹	m.p. (^°C)	Yield (%)	Calculated. (found)			IR (KBr, cm⁻¹)	Mass (FAB+) (m/z) ()	¹H NMR (CDCl₃, δ)
Compound	R	R¹	m.p. (^°C)	Yield (%)	C	H	N			¹H NMR (CDCl₃, δ)

1a	Phthalimido	H	237–239	60	68.32 (68.30)	3.94 (3.97)	4.98 (4.95)	3540 (OH), 1700 (C=O acid), 1665 (C=O amide)	282	7.26–8.11 (m, ar-H, 8H), 4.21 (s, NCH₂, 2H), 11.2 (s, OH, 1H)

1b	Phthalimido methyl	H	100–102	50	69.15 (69.12)	4.44 (4.46)	4.74 (4.70)	3543 (OH), 1720 (C=O acid), 1665 (C=O amide)	296	7.25–8.21 (m, ar-H, 8H), 4.21 (m, NCH₂, 2H), 3.91 (m, ar-CH₂, 2H), 11.4 (s, OH, 1H)

1c	2-Phenyl-3-methyl-quinazolin (3H)4-one	H	130–132	55	74.58 (74.54)	4.90 (4.93)	7.56 (7.54)	3530 (OH), 1695 (C=O acid), 1685 (C=O quinazolone moiety), 1665 (C=O amide), 1642 (C=N)	371	7.12–8.25 (m, ar-H, 13H), 4.23 (m, NCH₂, 2H), 3.94 (m, ar-CH₂, 2H), 11.2 (s, OH, 1H)

1d	Nicotinamido	C₆H₅	118-119	65	72.28 (72.25)	4.85 (4.88)	8.43 (8.42)	3540 (OH), 3390 (NH), 1700 (C=O acid), 1656 (C=O amide), 1656 (C=N)	333	7.12–8.17 (m, ar-H, 13H), 8.15 (brs, CONH, 1H), 5.56 (s, CH, 1H), 11.0 (s, OH, 1H)

3a	Phthalimido	H	178–180	55	65.08 (65.03)	4.44 (4.48)	14.23 (14.20)	3316 (NH), 1665 (C=O amide)	296	10.43 (s, NH, 1H), 7.20 (brs, NH₂, 2H), 7.28–8.25 (m, ar-H, 8H), 4.21 (s, NCH₂, 2H),

3b	Phthalimido methyl	H	162–164	50	66.01 (66.00)	4.89 (4.91)	13.58 (13.53)	3210 (NH), 1667 (C=O amide)	310	10.43 (s, NH, 1H), 7.20 (brs, NH₂, 2H), 7.25–8.19 (m, ar-H, 8H), 4.26 (m, NCH₂, 2H), 3.93 (m, ar-CH₂, 2H).

3c	2-Phenyl-3-methyl-quinazolin (3H)4-one	H	114–116	55	71.86 (71.83)	5.24 (5.28)	14.57 (14.55)	3286 (NH), 1685 (C=O quinazolone moiety), 1665 (C=O amide), 1642 (C=N)	385	10.52 (s, NH, 1H), 7.25 (brs, NH₂, 2H), 7.42–8.29 (m, ar-H, 13H), 4.15 (m, NCH₂, 2H), 3.91 (m, ar-CH₂, 2H).

3d	Nicotinamido	C₆H₅	88–90	60	69.35 (69.30)	5.24 (5.27)	16.17 (16.14)	3390 (NH), 3310 (NH amido), 1669 (C=O amide), 1556 (C=N)	346	10.47 (s, NH, 1H), 7.23 (brs, NH₂, 2H), 8.35 (brs, CONH, 1H), 7.27–8.27 (m, ar-H, 13H), 5.58 (s, CH, 1H).

5a	Phthalimido	H	298-299	50	58.11 (58.07)	3.73 (3.77)	19.93 (19.90)	3390 (NH), 2568 (SH), 1660 (C=O amide), 1640 (C=N)	352	11.26 (s, SH, 1H), 7.15 (brs, NH₂, 2H), 7.24–8.23 (m, ar-H, 8H), 4.21 (s, NCH₂, 2H).

5b	Phthalimido methyl	H	208–210	45	59.16 (59.14)	4.14 (4.16)	19.17 (19.14)	3389 (NH), 2560 (SH), 1668 (C=O amide), 1645 (C=N)	366	11.31 (s, SH, 1H), 7.21 (brs, NH₂, 2H), 7.27–8.28 (m, ar-H, 8H), 4.24 (m, NCH₂, 2H), 3.93 (m, ar-CH₂, 2H).

5c	2-Phenyl-3-methyl-quinazolin (3H)4-one	H	146–148	55	65.44 (65.40)	4.58 (4.61)	19.08 (19.03)	3396 (NH), 2565 (SH), 1685 (C=O quinazolone moiety), 1656 (C=O amide), 1642 (C=N)	441	11.43 (s, SH, 1H), 7.27 (brs, NH₂, 2H), 7.33–8.25 (m, ar-H, 13H), 4.18 (m, NCH₂, 2H), 3.96 (m, ar-CH₂, 2H).

5d	Nicotinamido	C₆H₅	192–194	60	62.67 (62.63)	4.51 (4.55)	20.88 (20.85)	3396 (NH), 3315 (NH amido), 2568 (SH), 1665 (C=O amide), 1642 (C=N)	403	11.41 (s, SH, 1H), 7.22 (brs, NH₂, 2H), 7.18–8.23 (m, ar-H, 13H), 8.31 (brs, CONH, 1H), 5.54 (s, CH, 1H).

6a	Phthalimido	H	284-285	62	70.57 (70.53)	4.01 (4.05)	13.27 (13.24)	3350 (NH), 1663 (C=O amide), 1585 (C=N)	528	10.28 (brs, NH of thiadiazine, 1H), 6.91–8.23 (m, ar-H, 18H), 4.22 (s, NCH₂, 2H).

6b	Phthalimido methyl	H	>300	45	70.96 (70.92)	4.28 (4.30)	12.93 (12.90)	3356 (NH), 1660 (C=O amide), 1595 (C=N)	542	10.26 (brs, NH of thiadiazine, 1H), 7.12–8.21 (m, ar-H, 18H), 4.21 (m, NCH₂, 2H), 3.92 (m, ar-CH₂, 2H).

6c	2-Phenyl-3-methyl-quinazolin (3H)4-one	H	75-76	50	74.00 (73.97)	4.58 (4.61)	13.63 (13.61)	3360 (NH), 1680 (C=O quinazolone moiety), 1650 (C=O amide), 1585 (C=N)	617	10.24 (brs, NH of thiadiazine, 6.99–8.19 (m, ar-H, 23H), 4.28 (m, NCH₂, 2H), 3.99 (m, ar-CH₂, 2H).

6d	Nicotinamido	C₆H₅	298-299	57	72.64 (72.61)	4.53 (4.57)	14.52 (14.50)	3396 (NH), 1616 (C=O amide), 1556 (C=N)	579	10.29 (brs, NH of thiadiazine, 1H), 7.20–7.88 (m, ar-H, 23H), 8.15 (brs, CONH, 1H), 5.57 (s, CH, 1H).