110704-19-3

Basic information

• Product Name: Benzothiazole, 5-chloro-2-(chloromethyl)- (9CI)
• Synonyms: Benzothiazole, 5-chloro-2-(chloromethyl)- (9CI);5-Chloro-2-(chloroMethyl)-1,3-benzothiazole;5-chloro-2-(chloroMethyl)benzo[d]thiazole;2-Chloromethyl-5-chlorobenzothiazole
• CAS NO: 110704-19-3
• Molecular Formula: C₈H₅Cl₂NS
• Molecular Weight: 218.103
• Product Categories: BENZOTHIAZOLE
• Mol File: 110704-19-3.mol

Chemical Properties

• Melting Point: 102-104 °C
• Boiling Point: 310.6±22.0 °C(Predicted)
• Appearance: /
• Density: 1.494±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: -0.08±0.10(Predicted)
• CAS DataBase Reference: Benzothiazole, 5-chloro-2-(chloromethyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzothiazole, 5-chloro-2-(chloromethyl)- (9CI)(110704-19-3)
• EPA Substance Registry System: Benzothiazole, 5-chloro-2-(chloromethyl)- (9CI)(110704-19-3)

Safety Data

• Hazardous Substances Data: 110704-19-3(Hazardous Substances Data)

Upstream product

• 51076-95-0 2-chloro-1,1,1-triethoxyethane 
• 1004-00-8 4-chloro-2-aminobenzenethiol 
• 79-04-9 chloroacetyl chloride 
• 74974-54-2 2-chloro-1,1,1-trimethoxyethane 
• 20358-00-3 2-amino-5-chlorobenzothiazole 

Downstream Products

• 933738-03-5 (5-chlorobenzo[d]thiazol-2-yl)methanamine 
• 1138333-21-7 3-[(5-Chloro-1,3-benzothiazol-2-yl)methoxy]-2,6-difluorobenzenecarbonitrile 
• 143163-72-8 2-(bromomethyl)-5-chloro-1,3-benzothiazole 

Relevant articles and documents

Synthesis and antibacterial activity of 3-benzylamide derivatives as FtsZ inhibitors

The emergence and spread of multidrug-resistant strains of the human pathological bacteria are generating a threat to public health worldwide. In the current study, a series of PC190723 derivatives was synthesized and investigated for their antimicrobial activity. The compounds exhibited good activity against several Gram-positive bacteria as determined by comparison of diameters of the zone of inhibition of test compounds and standard antibiotics. Compound 9 with a fluorine substitution on the phenyl ring showed the best antibacterial activity in the series against M. smegmatis with the zone ratio of 0.62, and against S. aureus with the zone ratio of 0.44. The results from this study indicate that based on the unique 3-methoxybenzamide pharmacophore, compound 9 may represent a promising lead candidate against Gram-positive bacteria that are worthy of further investigation

SUBSTITUTED BENAMIDINES AS ANTIBACTERIAL AGENTS

Compounds of formula (IA) or (IB) have antibacterial activity: wherein W is ═C(H)— or ═N—; R3 is a radical of formula -(Alk1)m-(Z1)p-(Alk2)n-Q wherein m, p and n are independentl

Creating an antibacterial with in vivo efficacy: Synthesis and characterization of potent inhibitors of the bacterial cell division protein FTSZ with improved pharmaceutical properties

3-Methoxybenzamide (1) is a weak inhibitor of the essential bacterial cell division protein FtsZ. Alkyl derivatives of 1 are potent antistaphylococcal compounds with suboptimal drug-like properties. Exploration of the structure-activity relationships of analogues of these inhibitors led to the identification of potent antistaphylococcal compounds with improved pharmaceutical properties.

New 1,2,4-triazine derivatives and biological applications thereof

The invention relates to new 1,2,4-triazine derivatives of formula (I): wherein A, B, R2 and Y are defined in the application, their preparation and intermediates, their use as drugs and pharmaceutical compositions and associations containing them. The compounds of formula (I) are capable of inhibiting bacterial heptose synthesis.

ANTIBACTERIAL AGENTS

Compounds of formula (I) have antibacterial activity wherein R represents hydrogen or 1, 2 or 3 optional substituents; W is =C(R1)- or =N-; R1 is hydrogen or an optional substituent and R2 is hydrogen, methyl, or fluorine; or R1 and R2 taken together are -CH2-, -CH2CH2-, -O-, or, in either orientation, -O- CH2- Or -OCH2CH2-; R3 is a radical of formula -(Alk1)m-(Z)p-(Alk2)n-Q wherein m, p and n are independently 0 or 1, provided that at least one of m, p and n is 1, Z is -O-, -S-, -S(O)-, -S(O2)-, -NH-, -N(CH3)-, -N(CH2CH3)-, -C(=O)-, -O-(C=O)-, -C(=O)-O-, or an optionally substituted divalent monocyclic carbocyclic or heterocyclic radical having 3 to 6 ring atoms; or an optionally substituted divalent bicyclic heterocyclic radical having 5 to 10 ring atoms; Alk1 and Alk2 are optionally substituted C1C6 alkylene, C2-C6 alkenylene, or C2-C6 alkynylene radicals, which may optionally terminate with or be interrupted by -O-, -S-, -S(O)-, -S(O2)-, -NH-, -N(CH3)-, or -N(CH2CH3)-; and Q is hydrogen, halogen, nitrile, or hydroxyl or an optionally substituted monocyclic carbocyclic or heterocyclic radical having 3 to 6 ring atoms; or an optionally substituted bicyclic heterocyclic radical having 5 to 10 ring atoms.

Highly selective aldose reductase inhibitors. II. Optimization of the aryl part of 3-(arylmethyl)-2,4,5-trioxoimidazolidine-1-acetic acids

Accumulation of intracellular sorbitol, the product of glucose reduction catalyzed by aldose reductase (AR) [EC 1.1.1.21], is thought to be the main culprit in the development of diabetic complications. A series of 3- arylalkyl-2,4,5-trioxoimidazolidine-1-acetic acids was prepared and tested for inhibitory activities towards AR and aldehyde reductase (ALR) [EC 1.1.1.2]. These derivatives showed strong inhibitory activity against AR without markedly inhibiting ALR. In particular, the compounds with 3- nitrophenyl, 4-chloro-3-nitrophenyl, and chloro-substituted benzothiazolyl groups as the aryl part showed powerful AR-inhibitory activity. The chloro- substituted benzothiazolyl compound showed an AR selectivity of more than 5000 fold.

Novel, potent aldose reductase inhibitors: 3,4-dihydro-4-oxo-3-[[5-(trifluoromethyl)-2-benzothiazolyl]methyl]-1- phthalazineacetic acid (zopolrestat) and congeners

A new working hypothesis that there is a hitherto unrecognized binding site on the aldose reductase (AR) enzyme with strong affinity for benzothiazoles was pursued for the design of novel, potent aldose reductase inhibitors (ARIs). The first application of this hypothesis led to a novel series of 3,4-dihydro-4-oxo-3-(benzothiazolylmethyl)-1-phthalazineacetic acids. The parent of this series (207) was a potent inhibitor of AR from human placenta (IC50 = 1.9 x 10-8 M) and was orally active in preventing sorbitol accumulation in rat sciatic nerve, in an acute test of diabetic complications (ED50 = 18.5 mg/kg). Optimization of this lead through medicinal chemical rationale, including analogy from other drug series, led to more potent congeners of 207 and culminated in the design of 3,4-dihydro-4-oxo-3-[[5-(trifluoromethyl)-2-benzothiazolyl]methyl]-1- phthalazineacetic acid (216, CP-73,850, zopolrestat). Zopolrestat was found to be more potent than 207, both in vitro and in vivo. Its IC50 against AR and ED50 in the acute test were 3.1 x 10-9 M and 3.6 mg/kg, respectively. Its ED50s in reversing already elevated sorbitol accumulation in rat sciatic nerve, retina, and lens in a chronic test were 1.9, 17.6, and 18.4 mg/kg, respectively. It was well absorbed in diabetic patients, resulting in high blood level, showed a highly favorable plasma half-life (27.5 h), and is undergoing further clinical evaluation. An assortment of synthetic methods used for the construction of benzothiazoles, including an efficient synthesis of zopolrestat, is described. Structure-activity relationships in the new series are discussed.