II a and II b

A= Br/NO2

4-(2-hydroxy-3-bromo/nitro-5-chlorophenyl)-6-(1’-propene)-2-iminophenyl-3,6- dihydro-1, 3-thiazine

Farooque Haider Zulfequar Haider synthesized 4-(2-hydroxy phenyl)-5-benzoyl-6-pheyl or 6-(4-alkoxy pheny)l or 6-( 4-dimethyl amino phenyl )-2-imino -6-H- 2,3- dihydro 1,3- thiazine (4a,4a’,4a’’,4a’’’) from 2- hydroxyacetophenone and 4-(2-hydroxy -5-methyl phenyl)-5-benzoyl-6- phenyl-2-imino-6H- 2,3 dihydro-1,3-thiazine and respected derivatives (4b,4b’,4b’’,4b’’’) from 2-hydroxy- 5- methyl acetophenone with thiourea. All these compounds were evaluated for Anti microbial activity against gram positive bacteria S. aureus and S. subtilus and gram negative becteria E.coli and P. aeruginosa. With increase in number of hetero atoms the antimicrobial activity increases in the same order for all tested gram positive and gram negative bacteria.³

4-(2-hydroxy substituted phenyl)-5-benzoyl -6-(3,4-disubstituted phenyl)-2-imino-6-H-2,3-dihydro-1,3-thiazine derivatives

Table No:1

S.no	Cpd. Code	R1	R2	R3
1	4a	H	H	H
2	4a’	H	OCH₃	H
3	4a’’	H	OCH₃	OCH₃
4	4a’’’	H	N(CH₃)₂	H
5	4b	CH₃	H	H
6	4b’	CH₃	OCH₃	H
7	4b’’	CH₃	OCH₃	OCH₃
8	4b’’’	CH₃	N(CH₃)₂	H

Hayam h. Sayed et al. synthesized pyrimido[2,1-b]1,3-thiazine derivatives by cyclizing 4,6-Diamino-1H-pyrimidine-2-thione. These compounds have been tested for their activity againest E. coli, S. aureus, M. phlei, B. subtilis, C. albicans, A. niger. Biological evaluation have shown that 6b and 7b were slightly active against the tested microorganisms.⁴

6,8-bis-(substituted benzylidene-amino)-3,4,6-trihydropyrimido-[2,1-b][1,3]-thiazin-2-one

6,8-bis-(substituted benzylidene-amino)-3-(4-chlorobenzylidene)-4,6-dihydropyrimido[2,1-b][1,3]-thiazin-2-one

Ibadur R siddique et al. synthesized 4,4-bis(4,7-diaryl-2,3,4,5,7-pentahydrothiazolo(4,5-d)(1,3)-thiazine-2,5-dithion-3-yl) bibenzyls (4a-j) derivatives in one pot involving Knoevenagel condensation followed by Michael Addition. They were screened for Antifungal Activity againest Fusarium oxysporum, penicillium citrinum comparing with grisieofulvin and dathane M-45 as standards. 4c, 4e, 4i, 4j have shown best antifungal activity.⁵

4,4’-bis[4”,7”-diaryl-2”,3”,4”,5”,7”-pentahydrothiazolo[4,5-d][1,3]-thiazine-2”,5”-dithion-3”-yl] bibenzyls

Compd	R’	R”	Compd	R’	R”
4a	C₆H₅	C₆H₅	4F	C₆H₅	p.CH₃OC₆H₄
4b	p.CH₃OC₆H₄	C₆H₅	4G	p.CH₃OC₆H₄	p.CH₃OC₆H₄
4c	m,p.(CH₃O)₂ C₆H₃	C₆H₅	4H	m,p.(CH₃O)₂ C₆H₃	p.CH₃OC₆H₄
4d	p.ClC₆H₄	C₆H₅	4I	p.ClC₆H₄	p.CH₃OC₆H₄
4e	p.NO₂.C₆H₄	C₆H₅	4J	p.NO₂.C₆H₄	p.CH₃OC₆H₄

Tarik El‐Sayed Ali et al.synthesized Some new sulfur‐nitrogen heterocyclic systems 1, 3‐thiazines incorporating acridine and 1, 2, 3, 4‐tetrahydroacridine. Structures of the new compound was established by elemental analyses and spectral data. The synthesized compound was evaluated in vitro for their antibacterial activities against Staphylococcus aureus (ATCC 25923) and Streptococcus pyogenes (ATCC 19615) as examples of Gram positive bacteria and Pseudomonas fluorescens (S 97) and Pseudomonas phaseolicola (GSPB 2828) as examples of Gram negative bacteria. It was also evaluated in vitro for their antifungal activities against the Fusarium oxysporum and Aspergillus fumigatus fungal strains. Agar‐diffusion technique was used. Cephalothin, Chloramphenicol and Cycloheximide were used as reference drugs for Gram positive bacteria, Gram negative bacteria and fungi respectively. The compound have shown near activity as the reference.⁶

S. P. Rathod et al. reported the synthesis of two series of compounds by reacting 2’-Hydroxy 3’, 5’-dichloro-4-ethyl chalcone and 2’-hydroxy-3’, 5’-dichloro-4-hexylchalcone with phenyl thiourea and diphenylthiourea giving 4-(2’-hydroxy-3’5’-dichlorophenyl)-6-(ethyl)-2-iminophenyl-1, 3-thiazine (5a), 4-(2’-hydroxy-3’, 5’-dichlorophenyl)-6-(ethyl)-2-iminophenyl-3-phenyl-1, 3-thiazene (6a) and 4-(2’-hydroxy-3’, 5’-dicholoro -phenyl)-6-hexyl-2-iminophenyl-1, 3-thiazene (5b) and 4-(2’-hydroxy-3’, 5’-dichlorophenyl)-6-(hexyl)-2-iminophenyl-3-phenyl-1, 3-thiazene (6b). The Antibacterial activities of these compounds were studied againest gram positive and gram-negative pathogens like E .Coli, S. aureus, P. aeruginosa, S. subtilus. gentamycine as a standard. Presence of phenolic group and N, S hetero atoms increase the antibacterial activity of compound from (5a-6a) and (5b-6b).⁷

4-(2’-hydroxy-3’, 5’-dichlorophenyl)-6-substituted-2-iminophenyl-3-substituted-1, 3-thiazene

Table No: 2

S.no	Compound Code	R	R₁
1	5a	-CH₂CH₃	H
2	5b	-CH₂CH₃	-C₆H₅
3	6a	- (CH₂)₅-CH₃	H
4	6b	- (CH₂)₅-CH₃	-C₆H₅

Varalakshmi Devi. Ket al. reported synthesis of novel chalcones which were prepared by the reaction of different benzaldehydes with various acetophenones and subsequent treatment with thiourea resulting in the formation of corresponding thiazines. All the new compounds have been characterized by IR, 1H NMR, MS and elemental analysis. The compounds were screened for the antibacterial activity againest cultures of two gram positive bacteria Bacillus cereus, Staphylococcus aureus and two Gram negative bacteria Escherichia coli and Proteus vulgaris using agar well diffusion method. Penicillin and Streptomycin were used as standard drugs. From the screened results, it is observed that the presence of chloro group at the phenyl ring increases the antibacterial activity. The activity is maximum in a compound with methoxy group at 4th position.⁸

2-Amino-4-substitutedphenyl-6-trisubstituted phenyl-1,3-thiazine derivatives.

Anti-inflammatory Activity

Srikanth Jupudi et al. synthesized various 1, 3-Thiazine derivatives were synthesized by reacting acetanilide derivatives with substituted aryl aldehydes to give chalcones (A & E) which are then cyclized by reacting with thiosemicarbazide to give 2-hydrazinyl 1,3-thiazine derivatives (B & F). The latter compounds were treated with substituted aryl aldehydesor ketones to give 2-arylidene hydrazinyl 1,3-thiazine derivatives (C & G). These derivatives (C & G) were refluxed with Glycine in ethanol / Vilsmeir-Hack reagent (DMF: PoCl3) giving 2-substituted Imidazolidin-4-one 1, 3-Thiazine derivatives (D1-4) and 2-substituted pyrazolyl 1, 3-Thiazine derivatives (H1-4) respectively. All the derivatives were screened for In-vitro Anti Inflammatory activity. It was revealed that all compounds have shown dose dependent significant activity when compared with standard drug Diclofenac Sodium.⁹

Table No:3

S. no	Cpd. Name	R	A	b	c	Cpd. Name	R	a	b	c
1	1a	H	H	H	H	2a	Cl	H	H	H
2	1b	H	H	Cl	H	2b	Cl	H	Cl	H
3	1c	H	H	-OCH₃	H	2c	Cl	H	-OCH₃	H
4	1d	H	-OCH₃	-OCH₃	H	2d	Cl	-OCH₃	-OCH₃	H
5	1e	H	-OCH₃	-OCH₃	-OCH₃	2e	Cl	-OCH₃	-OCH₃	-OCH₃
6	3a	CH₃	H	H	H
7	3b	CH₃	H	Cl	H
8	3c	CH₃	H	-OCH₃	H
9	3d	CH₃	-OCH₃	-OCH₃	H
10	3e	CH₃	-OCH₃	-OCH₃	-OCH₃

Antimicrobial and Anti-Inflammatory

C. Sanjeeva Reddy et al. synthesized series of novel bis-chalcones by the reaction of 5,5’-methylene-bis-salicylaldehyde with various acetophenones, subsequent treatment with thiourea or guanidine resulted to the corresponding bis-thiazines or bispyrimidines. All the new compounds have been characterized by IR, 1H NMR, MS and elemental analysis. The Antibacterial, Antifungal and Anti-inflammatory activities of the compounds have also been evaluated. The compounds 4a-f were screened for their antibacterial activity against human pathogenic bacteria Escherichia coli, Staphylococcus aureus and Bacillus subtilis. streptomycin/ neomycin was used as antibacterial standard. The compound 4b is highly active against all the three organisms. 4e is highly active against E. coli, S. aureus and compound 4f is highly active against E. coli, B. subtilis. The compound 4a is almost inactive against all the three organisms. The antifungal activity was compared with the known antibiotic fluconazole the compound 4e is highly active against C. albicans. Remaining compounds showed moderate activity. Compounds (4b, 4c) were screened for their anti-inflammatory activity using rat paw edema method. Ibuprofen was used as standard anti-inflammatory drug. These compounds showed 22.01, 42.02 % of inhibition respectively, whereas standard ibuprofen showed 44% of inhibition.¹⁰

2-(2-Amino-4-substituted phenyl-6H-1,3-thiazin-6-yl)-4-[3-(2-amino-4-phenyl-6H-1,3-thiazin-6-yl)-4-hydroxybenzyl] phenol derivatives

Table No:4

Sno.	Compound Name	R
1	4A	H
2	4B	4-OCH₃
3	4C	4-Cl
4	4D	4-NO₂
5	4E	4-Br
6	4F	2-Cl

R. Kalirajan et al. reported synthesis of some novel heterocyclic derivatives such as Thazines, Oxazines, Isoxazoles and Pyrazoles from various Chalcones. The synthesized compounds have been characterized by TLC, Elemental analysis, IR and 1H.NMR Spectroscopy. The synthesized compounds were subjected to antimicrobial screening by cup plate method for zone of inhibition. The Antibacterial activity was tested against various gram positive (B. subtilis, S. aureus) and Gram negative bacteria ( E.coli, K. pneumonia) and anti fungal activity against various fungal strains (C. albians, A. niger). They are compared with standard drugs Ampicillin and Ketoconazole and Anti-inflammatory activity by In-Vitro HRBC Membrane Stabilization method taking Ibuprofen as standard drug. Many of the compounds show comparable activity with that of standard (Ampicillin and Ketoconazole) and have highly significant activity when compared with standard drug Ibuprofen.¹¹

6-(3’,4’-disubstituted)- 2-amino-4-phenyl-1,3-thiazine derivatives

Table No:5

S.No	Cpd. Name	R1	R2	R
1	Ia	-OCH₃	H	-C₆H₅
2	IIa	H	- Cl	-C₆H₅
3	IIIa	H	- NO₂	-C₆H₅

R.H.Udupi et al. synthesized chalcones comprising diphenyl ether moiety by Claisen Schmidt condensation of 3-phenoxy benzaldehyde with substituted acetophenones. The characterization of new compounds has been done by means of IR, ¹ H NMR and Mass spectral data and elemental analysis. The Synthesized compounds screened for antitubercular, antibacterial, antifungal and anti-inflammatory activities.¹²

Anti cancer Activity

Wei Wang synthesized series of novel multithioether derivatives by the combining thiazoline and thiazine with dibromides and their structures were characterized by IR, 1H NMR, MS and elemental analysis. The synthesized derivatives were tested for antitumor activity. The in vitro antitumor activities of the synthesized target compounds were done against A-549 (human lung cancer cell) and Bcap-37 (human breast cancer cell) which were evaluated by the standard MTT assay. The data revealed that compound 5g possessed higher anti- tumor activities.¹³

1,2-Bis(4,5-Dihydro-1,3-thiazin-2-ylsulfanyl)alkanes

Asiye Meriç et al. synthesized 3,4-disubstituted-7,8-dihydro-6H-imidazo[2,1- b] [1,3] thiazines. The structures of imidazo[2,1-b][1,3]thiazine derivatives was confirmed by infrared (IR), ¹H-NMR, and ¹³C-NMR. The cytotoxicities of the synthesized compounds on both of noncancer (F2408) and cancer (5RP7) cells were measured by 3-(4,5-dimethyl-thiazollyl-2)-2,5-diphenyltetrazolium (MTT) assay.¹⁴

Anti-diabetic Activity

Beauchamp, Benardeau, Hilpert, Wang et al. reported use of aminodihydrothiazines as well as their pharmaceutically acceptable salts and pharmaceutical compositions containing them are used for the treatment or prevention of diabetes, particularly type 2 diabetes by selective inhibition of BACE2.¹⁵

Anti-Inflammatory, Analgesic and Ulcerogenic Activity

Vijay V. Dabholkar et al. reported synthesis of Series of chalcones and 2-substituted guanidino-4-(2'-amino-5'-substitued phenyl) mercapto-6-phenyl-1, 3-thiazine derivatives. The following were studied by IR, NMR and Mass spectroscopy. The new products showed Anti-inflammatory, Analgesic and Ulcerogenic activities comparable to that of Indomethacin and Acetylsalicylic acid respectively. It was revealed that 4a, 4d, 4e and 4f showed moderate anti-inflammatory activity 4d, 4e and 4f showed good to excellent analgesic activity and all compounds have shown mild ulcerogenic activity.¹⁶

2-(N-substituted)guanidino-4-(substituted- 2'-aminophenyl)mercapto-6-phenyl-1, 3-thiazine derivatives

Table No:6

S. No.	Cpd. Name	R1	R2
1	4a	H	H
2	4b	H	-C₆H₅
3	4c	H	P-OCH₃-C₆H₄
4	4d	H	P-Br-C₆H₄
5	4e	-CH3	H
6	4f	-CH3	-C₆H₅
7	4g	-CH3	P-OCH₃-C₆H₄
8	4h	-CH3	P-Br-C₆H₄

Anti-Inflammatory and Immunotropic Activity

Zawisza T et al. reported study of Anti-inflammatory and Immunosuppressive activity of a series of new derivatives of tetrahydro [1,3]- thiazines which were obtained as a result of condensation of some N, N¹-derivatives of thiocarbamide and malonyl dichlorides, depending on the reaction conditions and chemical character of reagents.1,3-thiazine derivatives, 5,5- diallyl -2- phenylimino-3- phenyl- 2, 3, 4, 5- tetrahydro- [1,3] -thiazine-4, 6-dione and 5,5-diethyl-2-phenylimino-3-naphtyl-2, 3, 4, 5 -tetrahydro-[1,3]- thiazine-4, 6-dione exhibited Anti-inflammatory activity. The compounds also contained the immunotropic component, either stimulatory or suppressive, Some interdependence between chemical structure and biological activity in the group of the investigated 1, 3-thiazines derivatives was observed.¹⁷

5,5- diallyl -2- phenylimino-3- phenyl- 2, 3, 4, 5- tetrahydro- [1,3] -thiazine-4, 6-dione

5,5-diethyl-2-phenylimino-3-naphtyl-2, 3, 4, 5 -tetrahydro-[1,3]- thiazine-4, 6-dione

Anti anxiety, Anti convulsant and Spontaneous motor activity

Tadeusz s.jagodzinski et al. reported the reaction of 2-(β-hydroxyethyl)-pyrrolidine with isothiocyanates giving rise to thiourea derivatives which are cyclized on refluxing in hydrobromic acid to yield N-(3, 4, 4a, 5, 6, 7- hexahydro-1H- pyrrolo [1, 2-c] [1,3] thiazin-1-ylidene)-aryl (alkyl) amines. Compounds were screened for Antianxiety, Anticonvulsant and Spontaneous motor activities.¹⁸

N-(3,4,4a,5,6,7-hexahydro-1H-pyrrolo[1,2-c][1,3]thiazin-1-ylidene)-aryl(alkyl)amines

Tuberculostatic and Circulatory Activities

Foks H, Rudnicka W, Głowka M, Kaliszan R, Nasal A, Damasiewicz B, Radwańska A, Petrusewicz J, Trzeciak H, Okopień B, et al.synthesized a group of condensed triazole-thiazine derivatives were obtained in reaction of the corresponding 5-substituted 1,2,4-triazole-3-thiones with epichlorohydrin in alkaline medium. The structure of the compounds synthesized was confirmed by spectral and roentgenographic methods. Tuberculostatic and circulatory activities of the compounds were also studied.¹⁹

Miscellaneous Activities

Sina I. Odejinmi, Rafael G. Rascon, Manshu Tang, Hariprasad Vankayalapati and Kent Lai did structural activity studies on Classic Galactosemia which is a rare human disease associated with the accumulation of a toxic level of galactose-1-phosphate (gal-1P) caused by the inherited deficiency of galactose-1-phosphate uridyl transferase (GALT) activity. To reduce the toxic level of gal-1P in patients, identification is one by high-throughput screening, over 200 small molecule GALK inhibitors. 4-oxo-3,4-dihydro-2H-1,3-thiazine-5-carbonitrile scaffold have been selected for further structure activity relationship characterization, lead optimization with regards to potency and efficacy in order to reduce gal-1P accumulation in patient cells.²⁰

4-oxo-3,4-dihydro-2H-1,3-thiazine-5-carbonitrile

V. J. Hushare et al. synthesized three series of compounds by reacting 2-Hydroxy-3,5-dichloro acetophenone with three aldehydes like chlorobenzaldehyde, Nitrobenzaldehyde and butyraldehyde giving three compounds where they are reacted with Thiourea, Phenylthiourea and Diphenyl thiourea giving three series of compounds. Like 4-(2-hydroxy-3,5-dichlorophenyl)-6-(4-chlorophenyl)-2-imino-3,6- dihydro-1,3-thiazine (4a), 4-(2-hydroxy-3,5-dichlorophenyl)-6-(4-chlorophenyl)-2-imino phenyl -3,6-dihydro- 1,3-thiazine (5a) and 4-(2-hydroxy-3,5-dichlorophenyl)-6-(4-chlorophenyl)-2-iminophenyl-6-hydro-3-phenyl- 1,3-thiazine (6a). Growth promoting activity on some flowering plants viz. Papaver rhoeas, Dianthus chinensis, Candy tuft, Calendula officinalise, Gladiola tristis, Gaillardia is done. The experimental set up of the study was divided into I) Seed Treatment II) Field Experiment When the comparison of morphological characters was made between those of treated and control groups plants, it was interesting to note that all the plants exhibited significant shoot growth, and considerable increase in the number of leaves as compared to those of untreated ones.²¹

4-(2’-hydroxy-3’,5’-disubstituted)-6-(4’’-chlorophenyl)-2-substitutedimino-3,6-dihydro-1,3-thiazines

Where R= C6H5-NO2, C6H5-Cl, (CH2)3-CH3

1. For 4a,4b and 4c : R2=R3= H

2. For 5a,5b and 5c : R2= H, R3=C6H5-

3. For 6a, 6b and 6c: R2=R3= C6H5-

CONCLUSION:

1,3-thiazines are versatile molecules which require further research regarding synthesis and elucidation of mechanism of action of different derivatives by conducting invivo & invitro studies and QSAR development studies to bring the potential effects.

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