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A 3-substituted oxazole-fused caged dodecaborane compound and its preparation method and application

A technology of compounds and compositions, applied in the field of 3-substituted oxazole-fused caged dodecaborane compounds and their preparation, capable of solving unexplored problems

Active Publication Date: 2021-11-09
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, cycloaliphatic functional groups or nonaromatic functional groups as directing groups for the selective activation of B–H bonds have never been explored

Method used

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  • A 3-substituted oxazole-fused caged dodecaborane compound and its preparation method and application
  • A 3-substituted oxazole-fused caged dodecaborane compound and its preparation method and application
  • A 3-substituted oxazole-fused caged dodecaborane compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0109] Example 1 RV-02

[0110]

[0111] In the glove box, under the protection of inert nitrogen gas, prepare a dry 20mL small glass reaction bottle, add a stirring bar, add [Et 3 NH][B 12 h 11 NH 3 ] (0.80 mmol, 1 equiv) and NaH (2.5 mmol, 3.1 equiv). Ultra-dry THF (6 mL) was then added. Stir at 25°C for 30 minutes until stopped by hydrogen evolution. Menthyl chloroformate (0.9 mmol, 1.1 equiv) was dissolved in ultra-dry THF (1 mL) and added dropwise to the mixture via a plastic syringe over 30 minutes. The mixture was stirred for a further 2 hours at 25°C.

[0112] After the reaction was completed, the reaction bottle was moved outside to a fume hood. with [Et 3 NH]Cl solution (10mL H 2 O+2equiv[Et 3 NH]Cl) quenched the reaction; the pH at this point was about 7-8. Mixture with CH 2 Cl 2 / MeCN=4:1 (8×10 mL) extraction. The resulting organic layer was washed with MgSO 4 Dry, then filter and concentrate by rotary evaporation. The resulting mixed residue was...

Embodiment 2

[0123] Example 2 RV-03

[0124]

[0125] RV-03 was prepared according to the preparation method of Example 1, except that styrene was replaced by p-methylstyrene.

[0126] 1 H { 11 B}NMR (400MHz, CD 3 COCD 3 , 23°C): δ8.15 (br, 1H, NH anion), 8.09-7.70 (br, 1H, cation NH), 7.06-6.89 (overlap m, 4H, phenyl H), 4.78-4.66 (m, 1H , methyl CH), 3.50(q, J=7.4Hz, 6HN–CH 2 cation), 2.59-2.46(m,2H,B–CH 2 –CH 2 ),2.22(s,3Hphenyl-CH 3 ), 2.14-2.08 (overlap with solvent residual m, 1H, methyl CH), 2.03-1.88 (m, 1H, methyl CH), 1.74-0.39 (extensive overlap with m, 16H, 7-methyl CH and 9BH), 1.43 (t, J=7.3Hz, 9H, cation CH 3 ), 0.92-0.82 (overlap m, 6H, 2 methyl CH 3 ), 0.79 (d, J=6.9Hz, 3H, methyl CH 3 ),0.58-0.51(m,2H,B–CH 2 –CH 2 ).

[0127] 13 C{ 1 H}NMR (100MHz, CD 3 COCD 3 ,23°C): δ169.75 (C=N), 145.47, 134.26, 129.28, 128.45 (characteristic peak of phenyl), 82.93 (methyl CH), 48.13 (cation CH 2 ), 47.97 (methyl CH), 41.62, 36.94 (2 methyl CH 2 ), 34.52 (B–CH 2 –...

Embodiment 3

[0130] Example 3 RV-04

[0131]

[0132] RV-04 was prepared according to the preparation method of Example 1, except that styrene was replaced by methyl 4-vinylbenzoate.

[0133] 1 H { 11 B}NMR (400MHz, CD 3 COCD 3 ,23℃):δ8.17(br,1H,NH anion),7.85(d,J=7.7Hz,2H,phenyl H),7.24(d,J=7.7Hz,2H,phenyl H),4.80 -4.62(m, 1H methyl CH), 3.83(s, 3H, –COOCH 3 ),3.48(q,J=7.4Hz,6H,N–CH 2 cation), 2.67-2.56(m,2H,B–CH 2 –CH 2 ), 2.16-2.07 (overlap with solvent residual m, 1H, methyl CH), 1.96-1.86 (m, 1H, methyl CH), 1.77-0.41 (extensive overlap with m, 16H, 7CH and 9BH), 1.42 (t , J=7.2Hz, 9H, cation CH 3 ), 0.91 (d, J=8.2Hz, 3H, methyl CH 3 ), 0.87 (d, J=8.3Hz, 3H, methyl CH 3 ), 0.78 (d, J=6.7Hz, 3H, methyl CH 3 ),0.65-0.50(m,2H,B–CH 2 –CH 2 ). Only one N–H signal was clearly detected.

[0134] 13 C{ 1 H}NMR (100MHz, CD 3 COCD 3 ,23°C): δ169.59 (C=N), 167.43 (C=O), 155.05, 129.98, 128.75, 127.57 (characteristic peak of phenyl), 82.45 (methyl CH), 51.97 (COOCH 3 ), 48.11...

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Abstract

The invention discloses a 3-substituted oxazole-fused caged dodecaborane compound, a preparation method and application thereof. The structure of the 3-substituted oxazole fused caged dodecaborane compound is as shown in formula (I), and the R 1 Be menthyl or camphoryl; The R 2 for H, C 6‑20 Aryl, C 1‑15 Alkyl, ‑C(O)O‑C 1‑5 Alkyl or ‑C(O)O‑C 6‑20 Aryl, the C 6‑20 Aryl is optionally replaced by 1, 2 or 3 H, F, Cl, Br, I, OH, NH 2 , NO 2 , CN, C 1‑5 Alkyl, C 1‑5 Alkoxy, -O-C(O)-C 1‑5 Alkyl, ‑C(O)‑NH‑C 1‑5 Alkyl, ‑NH‑C(O)‑C 1‑5 Alkyl, ‑C(O)O‑C 1‑5 Alkyl, C 6‑20 Aryl or 5-12 membered heteroaryl substituted; said A + For metal cations, quaternary ammonium cations or phosphorus cations. The preparation method utilizes menthyl and camphoryl as a directing group, selectively activates the 3-position B-H bond, and prepares the compound of formula (I); the stereoselectivity is high, and the yield is good, which increases the chance of discovering new antibacterial drug candidates . The compound of formula (I) provided by the invention has high-efficiency and broad-spectrum antibacterial effects.

Description

technical field [0001] The invention relates to the field of antibacterial drugs, in particular to a 3-substituted oxazole-fused caged dodecaborane compound and a preparation method and application thereof. Background technique [0002] In recent decades, the emergence and spread of antibiotic-resistant pathogens have been accelerating, resulting in a rapid increase in the level of antibiotic resistance. At present, antibiotic resistance of pathogenic bacteria has become a global public health problem. Therefore, the discovery of novel bioactive molecules is crucial to address the looming challenges posed by emerging infectious diseases and pathophysiological disorders. [0003] The emergence of multidrug-resistant pathogens is a clinical threat that deserves attention. The overuse of antibiotics and poor sanitation further exacerbate multidrug-resistant strains of gut bacteria such as E. coli, Shigella, and Salmonella, as well as Neisseria gonorrhoeae, a gastrointestinal ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02A61K31/69A61P31/04B01J31/22C07C209/00C07C211/07
CPCA61P31/04B01J31/2295B01J2231/32B01J2531/822C07C211/07C07F5/027
Inventor 西蒙·杜特怀勒樊德冯·斯戴V·拉杰什张江临D·拉克什杨帆金宇捷
Owner ZHEJIANG UNIV
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