Dibenzo[b,f]oxepine Molecules Used in Biological Systems and Medicine
Abstract
:1. Introduction
2. Extracting Dibenzo[b,f]oxepines from Plants and Its Significance in Medicine
2.1. Pacharin
- a.
- the stem bark, stem wood, and roots of Bauhinia ungulate L. [7];
- b.
- c.
- the heartwood of Bauhinia racemosa Lamk. [10];
- d.
- the stem bark of Bauhinia aculeata L. [11];
- e.
- f.
- vine stems from Millettia dorwardi Collet Hemsl [14];
- g.
- the bark of Rhamnus caroliniana [15];
- h.
- the flowers of Cercis chinensis Bunge [16].
2.2. Bauhiniastatins 1–4
2.3. Bauhinoxepins A and B
2.4. Yagonine, Aristoyagonine
2.5. Secocularidine, Secocularine, Norsecocularidine
2.6. Secosarcocapnine, Norsecosarcocapnine, 4-Hydroxysecosarcocapnine
2.7. Artocarpol A, Artocarpols D-G (Figure 3)
2.8. Tournefolic Acid B, Tournefolic Acid B Methyl Ester, and Tournefolic Acid B Ethyl Ester (Figure 3)
2.9. The Physicochemical Approaches to Estimate Medical Activity
3. Biosynthesis of Dibenzo[b,f]oxepines
4. Structure of Dibenzo[b,f]oxepine and Synthesis of Dibenzo[b,f]oxepine Derivatives
- Wagner–Meerwein rearrangement [66]
- 3.
- Preparation from 2-halogenobenzaldehydes [71]
- 4.
- Intramolecular aromatic nucleophilic substitution SNAr [58]
- 5.
- Knoevenagel condensation [72]
- 6.
- Intramolecular McMurry reaction [74]
- 7.
- Mn(III)-based oxidative radical rearrangement [75]
- 8.
- Sequential Mizoroki–Heck reaction and Pd-catalyzed etherification [76]
- 9.
- Oxidative CH bond functionalization and ring expansion with TMSCHN2 [77]
5. Active Synthetic Dibenzo[b,f]oxepin Derivatives
6. Potential of Dibenzo[b,f]oxepines as Microtubule Inhibitors
7. The Perspective for Applications of Dibenzo[b,f]oxepine Derivatives
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Entry | Name of Compound | XLogP3-AA | TPSA [Ų] | Hydrogen Bond Donor Count | Hydrogen Bond Acceptor Count |
---|---|---|---|---|---|
1 | Pacharin | 3.6 | 58.9 | 2 | 4 |
2 | Bauhiniastatin 1 | 2.5 | 72.8 | 1 | 5 |
3 | Bauhiniastatin 2 | 3.5 | 68.2 | 2 | 5 |
4 | Bauhiniastatin 3 | 3.5 | 68.2 | 2 | 5 |
5 | Bauhiniastatin 4 | 3.6 | 58.9 | 2 | 4 |
6 | Bauhinoxepin A | 4.5 | 58.9 | 2 | 4 |
7 | Bauhinoxepin B | 5.5 | 58.9 | 2 | 4 |
8 | Yagonine | 2.6 | 74.3 | 0 | 6 |
9 | Aristoyagonine | 2.7 | 57.2 | 0 | 5 |
10 | Secocularidine | 3.8 | 51.2 | 1 | 5 |
11 | Secocularine | 4.2 | 40.2 | 0 | 5 |
12 | Secosarcocapnine | 4.2 | 40.2 | 0 | 5 |
13 | Norsecosarcocapnine | 3.7 | 49 | 1 | 5 |
14 | Artocarpol D | 5.4 | 58.9 | 2 | 4 |
15 | Artocarpol E | 7.9 | 69.9 | 3 | 4 |
16 | Artocarpol F | 5.1 | 77.4 | 2 | 6 |
17 | Tournefolic acid B | 2.8 | 107 | 4 | 6 |
18 | Tournefolic acid B methyl ester | 3.2 | 96.2 | 3 | 6 |
19 | Tournefolic acid B ethyl ester | 3.5 | 96.2 | 3 | 6 |
20 | Combretastatin A-4 | 3.7 | 57.2 | 1 | 5 |
Compound | Pharmacological Activities | Figure on Which the Structure Was Placed |
---|---|---|
1 | antipsychotic properties | Figure 4 |
2a–c | antipsychotic properties | Figure 4 |
3a–d | sedative, anticonvulsant, and anesthetic-enhancing properties | Figure 4 |
4 | anxiolytic properties | Figure 4 |
5a,b | anti-inflammatory activity | Figure 4 |
6 | AII (angiotensin II) receptor antagonist | Figure 4 |
7 | antiestrogenic agent (moderately active) | Figure 4 |
8 | phase 1 clinical trials with pediatric and adolescent congenital muscular dystrophy; reduce the level of high-level Tau protein | Figure 4 |
9 | strong inhibitory effect on the proliferation of breast cancer cells of the MDA-MB-231 line | Figure 4 |
13 | the strongest cytotoxic effect against HeLa and U87 cancerous cells lines | Figure 5 |
14 | the strongest cytotoxic effect against HeLa and U87 cancerous cells lines | Figure 5 |
15a–h | In silico studies showed that compounds 15a–h and 16a–h interact with the colchicine binding site in tubulin with a part of the dibenzo[b,f]oxepine, in a part of the azo switch, or both at the same time. | Figure 7 |
16a–h | Figure 7 |
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Krawczyk, H. Dibenzo[b,f]oxepine Molecules Used in Biological Systems and Medicine. Int. J. Mol. Sci. 2023, 24, 12066. https://doi.org/10.3390/ijms241512066
Krawczyk H. Dibenzo[b,f]oxepine Molecules Used in Biological Systems and Medicine. International Journal of Molecular Sciences. 2023; 24(15):12066. https://doi.org/10.3390/ijms241512066
Chicago/Turabian StyleKrawczyk, Hanna. 2023. "Dibenzo[b,f]oxepine Molecules Used in Biological Systems and Medicine" International Journal of Molecular Sciences 24, no. 15: 12066. https://doi.org/10.3390/ijms241512066