Green Synthesis of Novel Class of Benzazocine Derivatives, their Crystal Structures and Anticancer Activity
Нема приказа
Аутори
Ghalib, Raza MuradHashim, Rokiah
Sulaiman, Othman
Jawad, Ali
Mehdi, Sayed Hasan
Bogdanović, Goran A.
Trifunović, Srećko R.
Kawamura, Fumio
Ahamed, B. M. Khadeer
Majid, Amin Malik Shah Abdul
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
Background: Heterocyclic molecules have been synthesized by a green and facile strategy. These mole-cules contain a 8-membered azocine ring. The structures have been determined by spectral analysis and single crystal X-ray analysis. These compounds have anticancer activity. Method: A mixture of ninhydrin and acetone/ethylmethylketone in acetic acid in molar ratio 1: 1 were heated on water bath for 15 minutes. The reaction mixtures were dried on rotary evaporator and crystallized with chloro-form- n-hexane (1: 1 v/v) to give the colorless crystals of 1 And 2 respectively. Compounds 3 and 4 were synthe-sized by adding o-phenylenediamine to the completed reaction mixtures of 1 and 2 and each was further heated on water bath for 5 minutes. The dried reaction mixtures were chromatographed over a silica gel column and crystalized as 3 and 4. Results: This strategy resulted novel class of anticancer benzazocines (3 and 4). Conclusion: This method features mild reaction conditions and simple o...peration. The synthesis completes in two steps; from ninhydrin to 1 and 2 and from 1 and 2 to 3 and 4. The same basic skeleton of 3 and 4 and the same synthesis procedure clearly shows the general applicability of this reaction that is also proved enough by single crystal X-ray analysis and the strategy can be applicable for a wide range of other substrates. The obtained compounds are potential anticancer agents.
Кључне речи:
Synthesis / crystal structures / benzazocine / methylated molecules / anticancer activityИзвор:
Current Organic Synthesis, 2017, 14, 1, 127-136
DOI: 10.2174/1570179413666151218201848
ISSN: 1570-1794; 1875-6271
WoS: 000394378600008
Scopus: 2-s2.0-85020040875
Колекције
Институција/група
VinčaTY - JOUR AU - Ghalib, Raza Murad AU - Hashim, Rokiah AU - Sulaiman, Othman AU - Jawad, Ali AU - Mehdi, Sayed Hasan AU - Bogdanović, Goran A. AU - Trifunović, Srećko R. AU - Kawamura, Fumio AU - Ahamed, B. M. Khadeer AU - Majid, Amin Malik Shah Abdul PY - 2017 UR - https://vinar.vin.bg.ac.rs/handle/123456789/1431 AB - Background: Heterocyclic molecules have been synthesized by a green and facile strategy. These mole-cules contain a 8-membered azocine ring. The structures have been determined by spectral analysis and single crystal X-ray analysis. These compounds have anticancer activity. Method: A mixture of ninhydrin and acetone/ethylmethylketone in acetic acid in molar ratio 1: 1 were heated on water bath for 15 minutes. The reaction mixtures were dried on rotary evaporator and crystallized with chloro-form- n-hexane (1: 1 v/v) to give the colorless crystals of 1 And 2 respectively. Compounds 3 and 4 were synthe-sized by adding o-phenylenediamine to the completed reaction mixtures of 1 and 2 and each was further heated on water bath for 5 minutes. The dried reaction mixtures were chromatographed over a silica gel column and crystalized as 3 and 4. Results: This strategy resulted novel class of anticancer benzazocines (3 and 4). Conclusion: This method features mild reaction conditions and simple operation. The synthesis completes in two steps; from ninhydrin to 1 and 2 and from 1 and 2 to 3 and 4. The same basic skeleton of 3 and 4 and the same synthesis procedure clearly shows the general applicability of this reaction that is also proved enough by single crystal X-ray analysis and the strategy can be applicable for a wide range of other substrates. The obtained compounds are potential anticancer agents. T2 - Current Organic Synthesis T1 - Green Synthesis of Novel Class of Benzazocine Derivatives, their Crystal Structures and Anticancer Activity VL - 14 IS - 1 SP - 127 EP - 136 DO - 10.2174/1570179413666151218201848 ER -
@article{ author = "Ghalib, Raza Murad and Hashim, Rokiah and Sulaiman, Othman and Jawad, Ali and Mehdi, Sayed Hasan and Bogdanović, Goran A. and Trifunović, Srećko R. and Kawamura, Fumio and Ahamed, B. M. Khadeer and Majid, Amin Malik Shah Abdul", year = "2017", abstract = "Background: Heterocyclic molecules have been synthesized by a green and facile strategy. These mole-cules contain a 8-membered azocine ring. The structures have been determined by spectral analysis and single crystal X-ray analysis. These compounds have anticancer activity. Method: A mixture of ninhydrin and acetone/ethylmethylketone in acetic acid in molar ratio 1: 1 were heated on water bath for 15 minutes. The reaction mixtures were dried on rotary evaporator and crystallized with chloro-form- n-hexane (1: 1 v/v) to give the colorless crystals of 1 And 2 respectively. Compounds 3 and 4 were synthe-sized by adding o-phenylenediamine to the completed reaction mixtures of 1 and 2 and each was further heated on water bath for 5 minutes. The dried reaction mixtures were chromatographed over a silica gel column and crystalized as 3 and 4. Results: This strategy resulted novel class of anticancer benzazocines (3 and 4). Conclusion: This method features mild reaction conditions and simple operation. The synthesis completes in two steps; from ninhydrin to 1 and 2 and from 1 and 2 to 3 and 4. The same basic skeleton of 3 and 4 and the same synthesis procedure clearly shows the general applicability of this reaction that is also proved enough by single crystal X-ray analysis and the strategy can be applicable for a wide range of other substrates. The obtained compounds are potential anticancer agents.", journal = "Current Organic Synthesis", title = "Green Synthesis of Novel Class of Benzazocine Derivatives, their Crystal Structures and Anticancer Activity", volume = "14", number = "1", pages = "127-136", doi = "10.2174/1570179413666151218201848" }
Ghalib, R. M., Hashim, R., Sulaiman, O., Jawad, A., Mehdi, S. H., Bogdanović, G. A., Trifunović, S. R., Kawamura, F., Ahamed, B. M. K.,& Majid, A. M. S. A.. (2017). Green Synthesis of Novel Class of Benzazocine Derivatives, their Crystal Structures and Anticancer Activity. in Current Organic Synthesis, 14(1), 127-136. https://doi.org/10.2174/1570179413666151218201848
Ghalib RM, Hashim R, Sulaiman O, Jawad A, Mehdi SH, Bogdanović GA, Trifunović SR, Kawamura F, Ahamed BMK, Majid AMSA. Green Synthesis of Novel Class of Benzazocine Derivatives, their Crystal Structures and Anticancer Activity. in Current Organic Synthesis. 2017;14(1):127-136. doi:10.2174/1570179413666151218201848 .
Ghalib, Raza Murad, Hashim, Rokiah, Sulaiman, Othman, Jawad, Ali, Mehdi, Sayed Hasan, Bogdanović, Goran A., Trifunović, Srećko R., Kawamura, Fumio, Ahamed, B. M. Khadeer, Majid, Amin Malik Shah Abdul, "Green Synthesis of Novel Class of Benzazocine Derivatives, their Crystal Structures and Anticancer Activity" in Current Organic Synthesis, 14, no. 1 (2017):127-136, https://doi.org/10.2174/1570179413666151218201848 . .