Synthesis, X-ray crystal structure, DNA/protein binding and cytotoxicity studies of five α-aminophosphonate N-derivatives

Wang, Qing-Ming; Yang, Lijing; Ding, Hui; Chen, Xuanrong; Wang, Hua; Tang, Xin

doi:10.1016/j.bioorg.2016.10.007

Cited by 25 publications

(11 citation statements)

References 48 publications

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“…From Fig.1&2, two -O-CH 2 CH 3 groups, one C α atom, and a double bond O atom to form the tetrahedral geometries of P atoms. Besides, C α atoms were responsible for the existence of optically activity, similar to the early report [16,19,20].…”

Section: Crystal Structure Of 1 Andsupporting

confidence: 79%

“…When the -CH 2 CH 3 bonded to P was substituted by hydroxy group, the dihedral angle between the 2hydroxyphenyl and pyridine rings is 54.9 (1)° [21]. The bond lengths of C α -P and P=O were almost comparable to the similar structures [16,19,20,22]…”

Section: Crystal Structure Of 1 Andmentioning

confidence: 82%

“…Therefore, BSA could store and transport certain drugs and small . Therefore, target BSA for the design of drug have been paid to special aminophosphonate structure as the reported compound [16,19,20] are synthesized and characterized (Scheme 1 and Supplementary Information). identification of the compound confirmed by IR, EAs 1 H-NMR, 3 MS spectroscopy and X-ray single crystal diffraction (Supplementary Information Fig.…”

Section: (4-fluorophenyl) Methylphosphonate (C 17 H 20 Clfno 3 P -Hydmentioning

confidence: 99%

“…From Scheme 1, α-aminophosphonate were prepared by the early reported methods with certain modified [16,19,20]. First, aromatic amine and 20 mmol benzaldehyde derivative were added to of C 2 H 5 OH and allowed to react…”

Section: Synthesis Of α-Aminophosphonatementioning

confidence: 99%

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Synthesis, Crystal Structure and Interaction with Bovine Serum Albumin (BSA) of Two α-Aminophosphonic Acids Derivatives

Huang

Wang

2019

CSIJ

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Two α-amino-phosphonate derivatives (1 & 2) were synthesized and their compositions and structures were characterized by Elemental Analysis (EA), FT-IR Spectrascopy (FT-IR), Electrospray Ionization Mass Spectrometry (ESI-MS), Nuclear Magnetic Resonance (NMR, 1H, 13C and 31P) and X-ray crystallography. Compound 1 & 2 were crystallized in monoclinic system with the space group P2(1)/n and P2(1)/c, respectively. The interaction effects of two α-aminophosphonate derivatives (1 & 2) with BSA were investigated and the binding constants were 1.07 × 104 M-1, 1.68 × 104 M-1, respectively. Besides, the values of n were indicated that 1:1 complex was formed between BSA and 1&2.

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Section: Crystal Structure Of 1 Andsupporting

confidence: 79%

Section: Crystal Structure Of 1 Andmentioning

confidence: 82%

Section: (4-fluorophenyl) Methylphosphonate (C 17 H 20 Clfno 3 P -Hydmentioning

confidence: 99%

Section: Synthesis Of α-Aminophosphonatementioning

confidence: 99%

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Synthesis, Crystal Structure and Interaction with Bovine Serum Albumin (BSA) of Two α-Aminophosphonic Acids Derivatives

Huang

Wang

2019

CSIJ

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“…A number of α-aryl and N-aryl aminophosphonates were prepared by the reaction of the corresponding imines with diethyl phosphite in ethanol. Despite the rather long (12-24 h) reaction times, only moderate yields (30-64%) could be reached ( Figure 6.54) [118,119].…”

Section: Catalyst-free Pudovik Reactions In Solventsmentioning

confidence: 99%

6. Synthesis of α-aminophosphonates by the Kabachnik–Fields reaction and by the Pudovik reaction

Bálint¹,

Tripolszky²,

Tajti³

2018

Organophosphorus Chemistry

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α-Aminophosphonates are of significant importance due to their biological activity. The most widely applied synthetic routes towards α-aminophosphonates are the Kabachnik-Fields reaction involving the condensation of amines, oxo compounds and >P(O)H species, such as dialkyl phosphites, and the Pudovik reaction of imines and >P(O)H reagents. By the double Kabachnik-Fields reaction, bis(aminophosphonates) have also became available. This chapter summarizes the synthesis of α-aminophosphonates and related derivatives through the two main routes as described in the literature over the last five years.

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α‐Iminophosphonates: Useful Intermediates for Enantioselective Synthesis of α‐Aminophosphonates

et al. 2020

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A wide range of methods for the enantioselective synthesis of α‐aminophosphonic acid derivatives have been developed over the years. Although the most used methodology is the Pudovik reaction, the use of α‐iminophosphonates for the synthesis of optically active α‐aminophosphonates has emerged during the last years. The existing methods for the synthesis of α‐phosphorylated imines and their enantioselective reactions for the synthesis of enantio‐enriched α‐aminophosphonates are summarized in this review.

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Synthesis, X-ray crystal structure, DNA/protein binding and cytotoxicity studies of five α-aminophosphonate N-derivatives

Cited by 25 publications

References 48 publications

Synthesis, Crystal Structure and Interaction with Bovine Serum Albumin (BSA) of Two α-Aminophosphonic Acids Derivatives

Synthesis, Crystal Structure and Interaction with Bovine Serum Albumin (BSA) of Two α-Aminophosphonic Acids Derivatives

6. Synthesis of α-aminophosphonates by the Kabachnik–Fields reaction and by the Pudovik reaction

α‐Iminophosphonates: Useful Intermediates for Enantioselective Synthesis of α‐Aminophosphonates

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