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The Synthesis of Chiral Compounds of Biological and Synthetic Interest Using Anhydride of L-Tartaric Acid

Thesis Info

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Author

Khan, Sher Wali

Program

PhD

Institute

Quaid-I-Azam University

City

Islamabad

Province

Islamabad.

Country

Pakistan

Thesis Completing Year

2013

Thesis Completion Status

Completed

Subject

Chemistry

Language

English

Link

http://prr.hec.gov.pk/jspui/bitstream/123456789/2219/1/2769S.pdf

Added

2021-02-17 19:49:13

Modified

2024-03-24 20:25:49

ARI ID

1676727598339

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Chiral protected and deprotected amides were synthesized by using commercially available L-tartaric acid having two asymmetric centers and C2 axis of symmetry. In the synthetic sequence, diacid functionality of L-tartaric acid was protected as dimethyl ester and diol as 1,3-dioxolane. The partial hydrolysis of 1,3-dioxolane dimethyl ester gave the corresponding monoester. Monoester upon treatment with different substituted anilines gave desired amides (2a-2t). Amides (2a-2t) afforded compounds (3a-3t) with the aid of acetyl chloride in methanol. All the compounds were characterized by using sophisticated spectroscopic techniques including IR, 1H NMR, 13C NMR, EI-MS and elemental analysis. The structures of compounds 2g, 2r and 3i were also unambiguously confirmed by X-ray crystallography. Protected (2a-2l) and deprotected amides (3a-3l) were tested for their antimicrobial activities at different concentrations against different fungal and bacterial strains and were found effective. Monoaryl esters of L-tartaric acid (4a-4h) were prepared and processed further in Fries rearrangement. The structure of compound 4e in the series was also confirmed by X-ray crystallography. N-Linked glycopyranosides (10a-10e) and O-Linked glycopyranosides (11a-11e) were synthesized from monoester of L-tartaric acid. The synthesized compounds were confirmed with the aid of spectroscopic techniques. The structure of compound 11c in the series was supported by X-ray analysis. Antileishmanial activity of the glycopyranosyl amides (10a-10e) and glycopyranosides (11a-11e) was assayed which showed moderate to good activities. Synthesis of glycoconjugates (13a-13e) was carried out by using glycopyranosyl α-trichloroacetimidates and dimethyl-L-tartrate. Chiral imides and amides were prepared from diacetyl-L-tartaric acid anhydride and aliphatic, substituted aromatic amines and amino acids. The imides (14g-14m) were subjected for their antifungal and antibacterial activities against different fungal and bacterial strains. All the compounds showed good antifungal and moderate to good antibacterial activities.
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جریبِ حیات

جریب حیات(افسانہ)

ڈاکٹر مجاہد عباس ،لیکچرر، نمل یونیورسٹی اسلام آباد

جریب زمین کے لیے ہے یا حیات کے لیے،  زمین اور حیات دونوں ہی اس سے ناواقف رہتی ہیں۔ البتہ انسان جو زمین سے اگایا جاتا ہے اور پھر زمین میں ہی دبایا جاتا ہے جریبوں کی  پیمائش بن کے رہ جاتا ہے۔

اقصیٰ کےلبوں پر  سَرمیلی بسنت کے پھول کھل رہے تھے۔اُس نے  زمین کی طرف جھکتے ہوئے اپنی زلف ِ دراز کو بائیں کان  کی اوٹ میں سُلا دیا اور زمین پر گرے کاغذ کو ہتھیلی پر رکھ کر دل میں اُتار لیا۔ اُسے اپنے پیلے لباس  کی مہک  وصل  کی چاندنی رات کا قصہ ِ ناتمام سنارہی تھی مگر وہ مسلسل سوچوں کی جریب سے پرائے موریے اور بورنیو کے جنگلات کی پیمائش کر رہی تھی۔وہ اُن جنگلات کے سحر انگیز مناظر میں یوں کھوئے جا رہی تھی  جیسے دین و دنیا کی متاع ِ بے پایاں اُسے نصیب ہو گئی ہو۔وہ ایک ایک پودے کے ایک ایک پتے کے ایک ایک  ملائم اور تیزکنارے کو چھو کر  اس کی خوشبو اور لطافت کو  جذب کر رہی تھی۔ وہ  خود کو  پرسکون سبز سمندر کی کشتی  سمجھ کر ہوا کے رخ پر دھیرے دھیرے رواں دواں تھی۔ ابھی اُس نے اپنی کمر سیدھی نہیں کی تھی کہ اسےگلی سے گزرتی ہوئی لاری کی آواز سنائی دی جس پر اے کلاس چنیوٹی فرنیچر  سلیقے سے لادا گیا تھا۔

 اس  نے ٹیَلوں لگے فرش سے پلاسٹک کی میز اور کرسیاں اٹھا کر گھر کی پچھلی طرف لان میں رکھ دیں جہاں پھولوں کے احاطے میں سبزے کی بہار تھی۔  یہ لان اس کی زندگی میں افضال کی طرح  اہمیت رکھتا تھا۔ وہ جب بھی تھک جاتی تو وہاں آرام کرتی تھی، پودوں...

ایڈورٹائزنگ کی مختلف صورتیں اور اسلامی تعلیمات

Media has wide spectrum in modern world such that it is known as fourth pillar of state. Media has made convenient and has provided numerous facilities. Apart from this media also has shortcoming. Media has wide application in modern world and it is used for different purposes but it has influenced the field of business significantly. In field of business there are various methods to advertise their products and goods but the role of media cannot be neglected nowadays. The owners of industries and factories find it the most suitable ways of enhancing the sale of their products and goods. Therefore advertising has become the most profitable and productive source of income because every company spend a huge amount in order to advertise their products. The Islam has allowed the human being to widen their business through fair means but it is necessary to analyze the Islamic and moral perspective of advertisement so that Muslims may know about the limitation of issue and under its constraints they can be benefited. In this article we will elaborate the Islamic significance and limitations of advertising.

Studies on Dissolution and Prevention Effects of Hajrul Yahood, Sang Sarmahi, Phyllanthus Niruri on Calcium Containing Kidney Stones in Rats.

Nephrolithiasis has severe ramifications with respect to health and management cost. Current modalities of treatment though very effective in getting provisional relief from stones are not devoid of side effects and also fail to avert the recurrence, which is in fact the main concern of patients with kidney stones. Hajrul yahood, Phyllanthus niruri and Cystone have been used in folk medicine since ages and are well known for their lithotriptic and anti- urolithic properties. The present study was carried out at the animal house of Sindh Agriculture University Tando Jam to evaluate the litholytic and anti -urolithic effects of Hajrul yahood, Sang sarmahi, Phyllanthus niruri and cystone on glyoxylate induced nephrolithiatic rats. For this purpose, seventy eight male wistar rats were equally divided into thirteen groups of six rats each. Hajrul yahood, Sang sarmahi and Phyllanthus niruri were administered either alone or in combination of equal quantity of each by weight. Cystone given alone was also utilized as a standard drug to compare the effects of Hajrul Yahood, Sang Sarmahi and Phyllanthus Niruri on calcium oxalate kidney stones. Calcium oxalate crystallization was induced by intraperitoneal injections of Glyoxalate prior to start of the treatment in the litholytic groups and was administered along with the test drugs in the groups. At the completion of treatment period, serum samples from 42 rats in groups; and both the kidneys from all the experimental rats were recovered. Serum was analyzed for the activity of anti-oxidant enzymes superoxide dismutase (SOD), glutathione peroxidase (GPX), catalase (CAT); and levels of calcium, magnesium, oxalate and creatinine. Right kidney was homogenized with phosphate buffer saline (PBS), and centrifuged. Supernatant thus obtained was analyzed for the levels of SOD, GPX, CAT, reduced glutathione (GSH) and malondialdehyde (MDA). The left kidney was fixed in Bouin liquid, embedded in paraffin, sectioned and stained with hematoxylin and eosin H&E for histological examination under polarized light microscope. Serum analysis results showed that the activity of antioxidant enzymes and magnesiumlevel in rat groups treated with cystone, combination, HY and PN were lower in the order given as against the negative controls, but were significantly higher than that of the positive controls (p<0.05). Serum calcium level was found to be in normal range in cystone, combination, HY and PN treated groups of rats, but it was lower than normal in positive controls. Both serum oxalate and creatinine levels were detected to be significantly lower in cystone, combination, HY and PN treated groups of rats as compared with positive controls. A similar comparison of the parameters measured in tissue samples revealed that antioxidant enzyme activities and reduced glutathione level were significantly enhanced in cystone, combination, HY, and PN treated groups of rats as against the positive controls. In contrast, tissue MDA levels were seen to be significantly lower in cystone, combination, HY and PN treated groups of rats than the positive controls. Histological findings of renal tissue sections were also consistent with the serum and tissue chemistries showing lesser damage to the kidney tissue and calcification in cystone, combination and HY treated groups of rats as against the positive controls. Cystone in comparison to combined treatment exhibited better nephro-protection against hyperoxaluria induced oxidative stress because of its increased antioxidant enzyme activities and increased glutathione and magnesium levels. In conclusion, present study has demonstrated the litholytic,and nephroprotective effects of cystone, HY and PN due to their high antioxidant capacity to inhibit lipid peroxidation in glyoxylate induced hyperoxaluric rats and also due to their ability to reduce oxalate synthesis. Sang sarmahi however, in contrast to the general notion has failed to exhibit any significant litholytic and anti urolithic effects at the dose used in present study.