619-86-3Relevant articles and documents
Synthesis and mesomorphic properties of bis ester derivatives of coumarin containing chalcone linkage
Shah, Priyanka,Soni, Rina,Soman, Shubhangi S
, (2021/05/04)
Bis ester derivatives of coumarin containing chalcone linkage with various terminal alkoxy groups were designed, synthesized and characterized. Compounds 11a-m were studied for their mesomorphic properties using polarizing optical microscope & differential scanning calorimetry and photophysical properties using UV-vis & fluorescence spectroscopy. In this particular homologous series, compounds having lower flexible alkoxy chains showed very good mesogenic property with nematic mesophase formation, while analogues with higher chains failed to show any liquid crystalline property. Compound 11a with methoxy group showed very good absorbance and fluorescence as compared to higher chain length analogues.
Synthesis, mesomorphic properties and biological evolution of calamitic-shaped chalcone-based LCs: effect of lateral and terminal group
Dwivedi, Durgesh J.,Thakor, Akshay,Desai, Vipul,Sharma, Vinay S.,Patel
, p. 16 - 32 (2021/05/26)
The mesomorphic properties of linear shaped homologous series based on two linkage group have been designed and synthesized with different side chain substituents (-OR) on the one end of terminal side with presence of lateral nitro group and second terminal iodo substituted group. Novel series consists thirteen members (C1 to C8, C10, C12, C14, C16, C18). Compounds (C1 to C6) showed nonliquid crystalline properties while compound (C7 to C18) displayed smectic and nematogenic mesophase properties. The textures of smectic C and nematic phase are fan, schlieren and droplets type. All these compounds were characterized by spectroscopic techniques such as [FTIR] and 1H Nuclear magnetic resonance [NMR] spectroscopy. The mesomorphic properties of these compounds were observed by POM and further confirmed by DSC and XRD. Chalconyl ester based compounds (C3 to C12) shows good antibacterial as well as antifungal activity compared with corresponding standard drugs.
Novel ester derivative of cinnamates with different long alkoxy chain: synthesis, mesomorphic properties, biological evaluation
Bhalodiya, Pradip C.,Patel, Hemant N.,Parmar, Tejasvi H.,Sangani, Chetan B.,Rajani, Dhanji P.
, p. 1 - 25 (2021/07/07)
A novel series of liquid crystals involving cinnamate-based mesogenic units interlinked between aromatic ester and alkyl bromide were designed and synthesized. All target molecules were confirmed by IR, 1H NMR, 13C NMR, ESI-MS, and elemental analysis. The mesomorphic behavior of novel synthesized materials (P1–P18), (V1–V18), and (M1–M18) was investigated through a polarizing optical microscope, differential scanning calorimetry, and thermogravimetric analysis (TGA) analysis. The lower carbon chain substituted member showed nematic phase while compound possess higher carbon chain exhibited only SmC phase. Thermal stability is determined by TGA analysis. All the cinnamate derivatives were screened for their anti-microbial, anti-malarial, and anti-tuberculosis potency. Among them, most of the derivatives exhibited outstanding anti-bacterial and anti-tuberculosis activity. Some derivatives also exhibited potent anti-fungal activity.
λ-shaped to T-shaped azo diester mesogens having methyl (–CH3)/methoxy(–OCH3) terminal substituents with trisubstituted benzene
Duan, Yongtao,Koshti, Rohit R.,Kumar Ameta, Rakesh,Patel, H. N.,Sangani, Chetan B.,Tarpada, Umesh P.,Vyas, Akshay,Yao, Yongfang
, (2021/07/12)
A two new homologous series of λ-shape to T-shape mesogenic azo diesters were synthesized, and their thermotropic properties were studied by differential scanning calorimetry and a hot-stage polarizing optical microscope. The difference between these two series is in the structure of terminal substituents methyl (–CH3) for series I and methoxy (–OCH3) for series II at one terminus. Structure variation from λ-shape to T-shape as we go from lower members to higher members is discussed. In the series I, methoxy to n-pentyloxy derivatives are non-mesogenic. n-hexyloxy derivative exhibits only monotropic nematic mesophase. n-heptyloxy to n-dodecyloxy derivatives exhibit monotropic smectic C mesophase. n-tetradecyloxy derivative exhibits enantiotropic SmA mesophase, whereas n-hexadecyloxy derivatives exhibit monotropic Smectic A mesophase. In series II, methoxy to n-hexyloxy derivatives are non-mesogenic. n-heptyloxy and n-octyloxy derivatives exhibit monotropic smectic C mesophase. Smectic A mesophase commences from the n-decyloxy derivative as a monotropic and persists up to the last member synthesized. The mesomorphic properties of the present series were compared with each other and with the structurally related mesogenic homologous series to evaluate the effect of methyl (–CH3)/methoxy (–OCH3) substituents as well as variation in the shape of the molecule by varying the alkoxy chain length of the bulky lateral substituent on mesomorphism.
Discovery of benzamide-hydroxypyridinone hybrids as potent multi-targeting agents for the treatment of Alzheimer's disease
Bai, Renren,Gu, Jinping,Guo, Jianan,Jiang, Xiaoying,Xie, Yuanyuan,Zhang, Changjun,Zhou, Tao
, p. 2045 - 2054 (2021/10/08)
A novel class of benzamide-hydroxypyridinone (HPO) derivatives were innovatively designed, synthesised, and biologically evaluated as potential multitargeting candidates for the treatment of Alzheimer's disease (AD) through pharmacophores-merged approaches based on lead compounds 18d, benzyloxy phenyl analogs, and deferiprone (DFP). These hybrids possessed potent Monoamine oxidase B (MAO-B) inhibition as well as excellent iron chelation, with pFe3+ values ranging from 18.13 to 19.39. Among all the compounds, 8g exhibited the most potent selective MAO-B inhibitor (IC50 = 68.4 nM, SI = 213). Moreover, 8g showed favourable pharmacokinetic properties and had great potential to penetrate the BBB in silico and PAMPA-BBB assay. Molecular modelling showed that 8g could adopt an extended conformation and have more enhanced interactions with MAO-B than 18d. In vitro and in vivo assays demonstrated that 8g remarkably resisted Aβ-induced oxidation and ameliorated cognitive impairment induced by scopolamine. Taken collectively, these results suggest that compound 8g is a potential multifunctional candidate for anti-AD treatment.
Cleavage of Carboxylic Esters by Aluminum and Iodine
Sang, Dayong,Yue, Huaxin,Fu, Yang,Tian, Juan
, p. 4254 - 4261 (2021/03/09)
A one-pot procedure for deprotecting carboxylic esters under nonhydrolytic conditions is described. Typical alkyl carboxylates are readily deblocked to the carboxylic acids by the action of aluminum powder and iodine in anhydrous acetonitrile. Cleavage of lactones affords the corresponding ω-iodoalkylcarboxylic acids. Aryl acetylates undergo deacetylation with the participation of the neighboring group. This method enables the selective cleavage of alkyl carboxylic esters in the presence of aryl esters.
Synthesis, biological activity, molecular docking studies of a novel series of 3-Aryl-7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives as the acetylcholinesterase inhibitors
Jin, Zhe,Zhang, Chao,Liu, Miao,Jiao, Simeng,Zhao, Jing,Liu, Xiaoping,Lin, Huangquan,Chi-cheong Wan, David,Hu, Chun
, p. 2478 - 2489 (2020/04/27)
The acetylcholinesterase inhibitors play a critical role in the drug therapy for Alzheimer’s disease. In this study, twenty-nine novel 3-aryl-7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives were synthesized and assayed for their human acetylcholinesterase (hAChE) inhibitory activities. Inhibitory ratio values of seventeen compounds were above 55% with 4c having the highest value as 77.19%. The compounds with the halogen atoms in the aromatic ring, and N,N-diethylamino or N,N-dimethylamino groups in the side chains at C-3 positions exhibited good inhibitory activity. SAR study was carried out by means of molecular docking technique. According to molecular docking results, the common interacting site for all compounds were found to be peripheral anionic site whereas highly active compounds were interacting with the catalytic active site too. HIGHLIGHTS A novel series of 3-aryl-7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives were synthesized and assayed for their human acetylcholinesterase (hAChE) inhibitory activities. The SAR study of the target 3-aryl-7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives was summarized. The active sites in the acetylcholinesterase were analyzed by molecular docking technique. Communicated by Ramaswamy H. Sarma.
1,3-Oxazine-2-one derived dual-targeted molecules against replicating and non-replicating forms of Mycobacterium tuberculosis
Velappan, Anand Babu,Kesamsetty, Dhanunjaya,Datta, Dhrubajyoti,Ma, Rui,Hari, Natarajan,Franzblau, Scott G.,Debnath, Joy
supporting information, (2020/10/02)
The high mortality rate and increasing prevalence of resistant Mtb are the major concerns for the Tuberculosis (TB) treatment in this century. To curtail the prevalence of resistant Mtb, we have prepared 1,3-oxazine-2-one based dual targeted molecules. Compound 67 and 68 were found to be equally active against replicating and non-replicatiing form of Mtb (MICMABA 3.48 and 2.97 μg/ml; MICLORA 2.94 and 2.15 μg/ml respectively). They had found to suppress the biosynthesis of alfa, methoxy and keto-mycolate completely, as well as inhibit enzymatic activity of MenG (IC50 = 9.11 and 6.25 μg/ml respectively for H37Ra; IC50 = 11.76 and 10.88 μg/ml respectively for M smegmatis).
2-Aryl benzazole derived new class of anti-tubercular compounds: Endowed to eradicate mycobacterium tuberculosis in replicating and non-replicating forms
Datta, Dhrubajyoti,Debnath, Joy,Franzblau, Scott G.,Ghosh, Kalyan Sundar,Hari, Natarajan,Ma, Rui,Rana, Shiwani,Velappan, Anand Babu
, (2020/09/04)
The high mortality rate and the increasing prevalence of Mtb resistance are the major concerns for the Tuberculosis (TB) treatment in this century. To counteract the prevalence of Mtb resistance, we have synthesized 2-aryl benzazole based dual targeted molecules. Compound 9m and 9n were found to be equally active against replicating and non-replicating form of Mtb (MIC(MABA) 1.98 and 1.66 μg/ml; MIC(LORA) 2.06 and 1.59 μg/ml respectively). They arrested the cell division (replicating Mtb) by inhibiting the GTPase activity of FtsZ with IC50 values 45 and 64 μM respectively. They were also capable of kill Mtb in non-replicating form by inhibiting the biosynthesis of menaquinone which was substantiated by the MenG inhibition (IC50 = 11.62 and 7.49 μM respectively) followed by the Vit-K2 rescue study and ATP production assay.
Green synthesis method of aromatic acid
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Paragraph 0048-0122; 0141-0146; 0271-0272, (2020/05/01)
The invention discloses a green synthesis method of aromatic acid. Nickel-catalyzed carbonyl insertion is carried out on aryl iodine in the presence of formate, acid anhydride, a phosphine ligand andan organic solvent by using a nickel catalyst to obtain the aromatic acid. Efficient catalytic conversion is realized by utilizing the cheap nickel catalyst, the reaction conditions are mild, and theoperation is simple.
