Synthesis and antimicrobial activity of some new 2-aminomethyl -5-(4-phenyl-5- mercapto-1,2,4-triazol-3-yl)methoxyindole derivatives

1070-10746-Bromo-2-bromometh yl-1-butyl-3-ethoxycarbonyl-5- ethoxycarbonylmethoxyindole 2 has been prepared from 2-methylindole derivative <b style="mso-bidi-font-weight: normal">1 using NBS as regioselective brominating agent in the presence of radical initiator like dihenzoyl peroxide. Compound 2 is then reacted with amines to yield corresponding 2-aminomethylindole diesters <b style="mso-bidi-font-weight: normal">3a-b. Hydrolysis of 3a-b by ethanolic sodium hydroxide gives the corresponding diacids 4a-b. Diesters <b style="mso-bidi-font-weight: normal">3a-b also react chemoselectively with excess of hydrazine hydrate (99 <span style="font-size:14.0pt;mso-bidi-font-size:8.0pt;font-family: Arial">%) to yield the corresponding monocarbohydrazides <b style="mso-bidi-font-weight: normal">5a-b instead of the expected dicarbohydrazides <b style="mso-bidi-font-weight: normal">6a-b. The  monocarbohydrazides 5a-b on reaction with phenylisothiocyanate followed by treatment with NaOH (4 %) solution afford the required 2-aminomethyl-5-(4-phenyl-5-mcrcapto- 1,2,4-triazol- 3-yl )methoxyindole derivatives <span style="font-size:14.0pt; mso-bidi-font-size:8.0pt;font-family:" times="" new="" roman";mso-fareast-font-family:="" "times="" roman";mso-ansi-language:en-us;mso-fareast-language:en-us;="" mso-bidi-language:ar-sa"="">5a-b<span style="font-size:14.0pt; mso-bidi-font-size:8.0pt;font-family:" times="" new="" roman";mso-fareast-font-family:="" "times="" roman";mso-ansi-language:en-us;mso-fareast-language:en-us;="" mso-bidi-language:ar-sa"="">. All the newly synthesised compounds are screened for their  antimicrobial activities.</span

Chemoselective reaction of benz[<i>g</i>]indole dicarboxylate towards hydrazine hydrate: Bisheterocycles: Synthesis and antimicrobial activity of some new 1-[2-hydroxyethyl]-3-ethoxycarbonyl-5-oxadiazolyl/triazolyl/ pyrrolylaminocarbonylmethoxy-2-methylbenz[<i>g</i>]indoles

794-800The exclusive formation of 1-[2-hydroxyethyl]-3-ethoxycarbonyl-2-methyl benz[g] indol-5-yloxyacetic acid hydrazide 6 from 1-[2-hydroxyethyl]-3-ethoxycarbonyl-5-methoxycarbonylmethoxy-2-methylbenz[g]indole 3 revealed the chemo­selectivity of the C5-ester over C3-ester towards nucleophilic attack of hydrazine hydrate. This monocarbohydrazide 6 is reacted separately with CS2/KOH, acetonyl acetone and isothiocyanates to secure the desired 1-[2-hydroxyethyl]-3-ethoxycarbonyl-5-(5-mercapto-1,3,4,-oxadiazl-2-y1)methoxy-2-methylbenz[g]indole 7, 1-[2-hydroxyethyl]-3-ethoxy-carbonyl-5-(2,5-dimethylpyrrol-1-yl)aminocarbonylmethoxy-2-methylbenz[g]indole 8 and 1-[2-hydroxyethyl]-3-ethoxy­carbonyl-5-(N-substituted thiosemicarbazinocarbonyl)methoxy-2-methylbenz[g]indole 9a-c. These thiosemicarbazides 9a-c are reacted with 4% NaOH to produce the 1-[2-hydroxyethyl]2-methybenz[g]indol-5-(4-substituted-5-mercapto-1,2,4-triazol-3-yl)methoxy-3-caboxylic acids 10a-c. All theses newly synthsised compounds are screened for their antimicrobial activities

Chemoselective reaction of indole 1,3-dicarboxylates towards hydrazine hydrate: Bisheterocycles: Synthesis and antimicrobial activity of some new 2-methyl-3-ethoxycarbonyl-1-oxadiazolyl/thiazolidinonyl/pyrrolyl­aminocarbonylmethylindoles

1663-1668Chemoselectivity of 1-ester over C3-ester of the indole dicarboxylates 3a,b towards the nucleophilic attack of hydrazine hydrate has been evidenced by the exclusive formation of 1-hydrazinocarbonylmethyl-3-ethoxycarbonyl-5-substituted-2-methylindoles 5a,b which have been further reacted separately with CS2/KOH, p-chlorobenzaldehyde and acetonyl acetone to furnish the 1-(5-mercapto-1,3,4-oxadiazol-2-yl)methyl-3-ethoxycarbonyl-5-substituted-2-methylindoles 6a,b, 1-p-Chlorobenzyl­idene­hydrazinocarbonylmethyl-3-ethoxycarbonyl-5-substituted-2-methylindoles 7a,b and 1-(2,5-dimethyl­pyrrol-1-yl)­amino­carbonylmethyl-3-ethoxycarbonyl-5-substituted-2-methylindoles 8a,b respectively. The Schiff’s bases 7a,b are reacted separately with thioglycolic acid to get the desired 1-(2-p-chlorophenyl-4-thiazolidinon-1-yl)aminocarbonylmethyl-3-ethoxycarbonyl-5-substituted-2-methylindoles 9a,b. These newly synthesised compounds are screened for their antibacterial and antifungal activities

1,3-Dipolar cycloaddition reactions: Synthesis and antimicrobial activity of novel 1-triazolylethylindole and 1-triazolylethylbenz[g]indole derivatives

1068-1073Indole azide 4 and benz[g]indole azide 12 are reacted separately with dimethyl acetylenedicarboxylate to secure the desired 1-[4,5-dimethoxycarbonyl-1,2,3-triazol-1-yl]ethyl-3-ethoxycarbonyl-5-methoxy-2-methylindole 5 and 1-[4,5-di­methoxy­carbonyl-1,2,3-triazol-1-yl]ethyl-3-ethoxycarbonyl-5-methoxy-2-methylbenz[g]indole 13, respectively. The reac­tion of indole azide 4 and benz[g]indole azide 12 with ethyl propiolate has been found to be regiospecific and produce only the 1-[4-ethoxycarbonyl-1,2,3-triazol-1-yl]ethyl-3-ethoxycarbonyl-5-methoxy-2-methylindole 6 and 1-[4-ethoxycarbonyl-1,2,3-triazol-1-yl]ethyl-3-ethoxycarbonyl-5-methoxy-2-methylbenz[g]indole 14, respectively. Indole azide 4 is also reacted with ethyl phenylpropolate to secure two isomeric products 1-[4-ethoxycarbonyl-5-phenyl-1,2,3-triazol-1-yl]ethyl-3-ethoxycarbonyl-5-methoxy-2-methylindole 8 and 1-[4-phenyl-5-ethoxycarbonyl-1,2,3-triazol-1-yl]ethyl-3-ethoxycarbonyl-5-methoxy-2-methylindole 9. All these newly synthesised compounds are screened for their antimicrobial activities

Synthesis and antimicrobial activity of new 1-n-butyl-3-acetyl-5-(2,4-diamino-1,3,5-triazin-6-yl)methoxy-2-methylindole derivatives

1226-12285-Hydroxyindole 1a is reacted with bromine in acetic acid to yield 6-bromo-5-hydroxyindole 1b. Compounds 1a-b are condensed with chloroacetonitrile in refluxing acetone in the presence of K2CO3 to obtain 3-acetyl-1-n-butyl-2-methylindol-5-yloxyacetonitriles 2a-b which are then reacted with dicyanodiamide in the presence of KOH in methanol and isopropanol to obtain the required 1-n-butyl-3-acetyl-5-(2,4-diamino-1,3,5-triazin-6-yl)methoxy-2-methylindoles 3a-b. All these new compounds have been screened for their antibacterial and antifungal activities.

On the Mechanism of Excitation Energy Transfer Involving Long and Short Range Interaction in Dilute Organic Liquid Scintillator Systems

The rate parameter K$\text{}_{3}$ of solvent-solute energy transfer and the rate parameter K$\text{}_{7b}$ for solvent-quencher energy transfer are determined experimentally under ultraviolet excitation for a system Ethyl 1 butyl-2-methyl-5 ethoxycarboxy methoxy indole-3-carboxylate (EBMEC) in a deoxygenated system comprising 1:9 mixture of toluene-cyclohexane as a function of temperature in the range of 20-70°C, using bromobenzene as a solvent quencher. The data is analysed in terms of compact equation formed by combining Voltz et al. and Birks and Conte models. The interaction distance for the energy transfer from the excited solvent to solute molecules and solvent to quencher molecules are determined using this equation. The magnitude of the interaction distance indicates that the excitation energy transfer takes place due to long-range interaction in the case of solvent-solute energy transfer and short-range interaction in the case of solvent quencher energy transfer in dilute systems

Chemoselectivity of indole-dicarboxylates towards hydrazine hydrate: Part III - Synthesis and antimicrobial activity of novel 4-thiazolidinonylindoles

156-159Exclusive formation of 3-carbethoxyindol-5-yloxyacetic acid hydrazides <b style="mso-bidi-font-weight: normal">3a,b from 3-carbethoxy-5- ethoxycarbonylmethoxyindoles 2a,b reveals the chemoselectivity of the C5-methyl ester function towards the nucleophilic attack of hydrazine hydrate. These mono hydrazides 3a,b on reacting with benzaldehydes furnish 1-alkyl-5- benzalhydrazinocarbonylmethoxy-3-ethoxycarbonyl-2-methylindoles 5a-h which on treatment with thioglycolic acid afford the desired 1-alkyl-3-ethoxycarbonyl-2-methyl-5-[(2-phenyl-4-thiazolidinon-3-yl)aminocarbonylmethoxy] indoles 6a-h. All the new compounds have been screened for their antibacterial and antifungal activities. </span

Chemoselective reaction of 1-<i>p</i>-acetanilido-3-acetyl-5-hydroxy-2-methylindole towards methyl chloroacetate :Synthesis and antiinflammatory activity of some new 5- pyrrolyl/oxadiazolyl/triazolyl/quinazolinylmethoxyindole derivatives

2023-20271-p-Acetanilido-3-acetyl-5-hydroxy-2-methylindole when treated with CH3I and K2CO3 in refluxing dry acetone produces N,O-methylated 1-p-N-methylacetanilido-3-acetyl-5-methoxy-2-methylindole but when it is reacted with methyl chloroacetate under similar reaction conditions yields only O-alkylated 1-p-acetanilido-3-acetyl-5-methoxycarbonylmethoxy-2-methylindole. This indole ester on treatment with hydrazine hydrate in refluxing ethanol gives only the monocarbohydrazide which is reacted separately with acetonyl acetone, triethyl orthoformate. CS2, KOH/N2H4.H2O, and 1,3-benzoxazine to secure pyrrolyl/oxadiazolyl/triazolyl and quinazolinylmethoxyindoles. Some of these new indole derivatives are screened for their antiinflammatoryactivity

<span style="font-size:12.0pt;font-family: "Times New Roman";mso-fareast-font-family:"Times New Roman";mso-ansi-language: EN-IN;mso-fareast-language:EN-IN;mso-bidi-language:AR-SA" lang="EN-IN">One pot synthesis of novel 5, 11-dioxo-6-methyl-5,9,10,11-tetrahydro-8<i style="mso-bidi-font-style: normal">H</i>-naphth[2,3:1,2]pyrrolizine and its 9-acetoxy analogue</span>

1123-11255, 11-dioxo-6-methyl-5,9,10,11-tetrahydro-8<i style="mso-bidi-font-style: normal">H-naphth[2,3:1,2]-pyrrolizine <span style="font-size:12.0pt; font-family:" times="" new="" roman";mso-fareast-font-family:"times="" roman";="" mso-ansi-language:en-in;mso-fareast-language:en-in;mso-bidi-language:ar-sa"="" lang="EN-IN">5a and its 9-acetoxy analogue <b style="mso-bidi-font-weight: normal">5b are prepared in a one-flask procedure by the reaction of L-proline 1a or 4-hydroxy-L-proline 1b with refluxing acetic anhydride and olefinic dipolarophile 1,4-naphthoquinone 4.</span