Citation: Hua-Quan Liu, De-Cai Wang, Fei Wu, Wei Tang, Ping-Kai Ouyang. Synthesis and biological evaluation of 5’-phenyl-3’H-spiro-[indoline-3,2’-[1,3,4]oxadiazol]-2-one analogs[J]. Chinese Chemical Letters, ;2013, 24(10): 929-933. shu

Synthesis and biological evaluation of 5’-phenyl-3’H-spiro-[indoline-3,2’-[1,3,4]oxadiazol]-2-one analogs

1.
a School of Pharmaceutical Science, Nanjing University of Technology, Nanjing 210009, China;
2.
b College of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, Nanjing 210009, China

Corresponding author: De-Cai Wang,
Received Date: 19 April 2013
Available Online: 24 May 2013

A series of 5'-phenyl-3'H-spiro[indoline-3,2'-[1,3,4]thiadiazol]-2-one analogs were synthesized and their Bcl-2 protein inhibitory activities were studied. The lead compound was originally identified using a fluorescence polarization-based competitive binding assay. Among the 10 compounds investigated, 1k showed good binding affinities to Bcl-xL and Mcl-1, with inhibition constants of 8.9 mmol/L and 3.4 μmol/L, respectively. While compound 1c achieved tight binding affinities to Bcl-xL (Ki = 0.16 μmol/L), has the potential to be a new lead compound.
- Synthesis,
- 5’-Phenyl-3’H-spiro[indoline-3,2’-[1,3,4]thiadiazol]-2-one,
- Bcl-2 family proteins,
- Cancer
1. [1]
  [1] P. Meier, A. Finch, G. Evan, Apoptosis in development, Nature 407 (2000) 796-801.
2. [2]
  [2] H. Okada, T.W. Mak, Pathways of apoptotic and non-apoptotic death in tumour cells, Nat. Rev. Cancer 4 (2004) 592-603.
3. [3]
  [3] F.H. Igney, P.H. Krammer, Death and anti-death: tumour resistance to apoptosis, Nat. Rev. Cancer 2 (2002) 277-288.
4. [4]
  [4] C. Tse, A.R. Shoemaker, J. Adickes, et al., ABT-263: a potent and orally bioavailable Bcl-2 family inhibitor, Cancer Res. 68 (2008) 3421-3428.
5. [5]
  [5] S. Kitada, M. Leone, S. Sareth, et al., Discovery, characterization, and structure-activity relationships studies of proapoptotic polyphenols targeting B-Cell lymphocyte/leukemia-2 proteins, J. Med. Chem. 46 (2003) 4259-4264.
6. [6]
  [6] A.G. Letai, Diagnosing and exploiting cancer's addiction to blocks in apoptosis, Nat. Rev. Cancer 8 (2008) 121-132.
7. [7]
  [7] J. Adachi, Y. Mori, S. Matsui, et al., Indirubin and indigo are potent aryl hydrocarbon receptor ligands present in human urine, J. Biol. Chem. 276 (2001) 31475-31478.
8. [8]
  [8] S.K. Bhattacharya, A. Chakrabarti, Dose related proconvulsant and anticonvulsant activity of isatin, a putative biological factor in rats, Indian J. Exp. Biol. 36 (1998) 118-121.
9. [9]
  [9] S.K. Bhattacharya, V. Glover, I. McIntyre, G. Oxenkrug, M. Sandler, Stress causes an increase in endogenous monoamine oxidase inhibitor (tribulin) in rat brain, Neurosci. Lett. 92 (1988) 218-221.
10. [10]
  [10] Y. Tian, S. Nam, L. Liu, et al., Spirooxindole derivative SOID-8 induces apoptosis associated with inhibition of JAK2/STAT3 signaling in melanoma cells, PLoS ONE 7 (2012) e49306.
11. [11]
  [11] L.L. Wang, J.J. Li, Z.B. Zheng, et al., Antitumor activities of a novel indolin-2-ketone compound, Z24: more potent inhibition on bFGF-induced angiogenesis and bcl-2 over-expressing cancer cells, Eur. J. Pharmacol. 502 (2004) 1-10.
12. [12]
  [12] W. Rzeski, J. Matysiak, M. Kandefer-Szerszeń, Anticancer, neuroprotective activities and computational studies of 2-amino-1,3,4-thiadiazole based compound, Bioorg. Med. Chem. 15 (2007) 3201-3207.
13. [13]
  [13] D.F. Aycock, G.R. Jurch Jr., Synthesis of alkyl trithioperesters (alkyl thiocarbonyl disulfides), J. Org. Chem. 44 (1979) 569-572.
14. [14]
  [14] N.K. Singh, S.B. Singh, A. Shrivastav, Antitumour and lmmmlomodulatory effects of Cu (Ⅱ) complexes of thiobenzyhdrazide, Met.-Based Drugs 9 (2002) 109-118.
15. [15]
  [15] C.S. Marvel, G.S. Hiers, Isatin, Org. Synth. 1 (1941) 327.
16. [16]
  [16] R. Bouhfid, N. Joly, M. Massoui, et al., An efficient synthesis of new spiro[indolo-3(1H), 20(30H)-oxadiazolyl] and 1-(triazol-4-ylmethyl)isatin derivatives, Heterocycles 65 (2005) 2949-2955.
17. [17]
  [17] M.G. Bursavich, A.M. Gilbert, S. Lombardi, et al., 5'-Phenyl-3'H-spiro[indoline-3,2'-[1,3,4]thiadiazol]-2-one inhibitors of ADAMTS-5 (Aggrecanase-2), Bioorg. Med. Chem. Lett. 17 (2007) 5630-5633.
18. [18]
  [18] Analytical data for compounds: 4: 24.0% yield, mp 78-80℃; ¹H NMR (300 MHz, DMSO-d₆): δ 12.09 (br s, ¹H), 7.71-7.69 (m, 2H), 7.45-7.38 (m, 3H), 6.23 (br s, 2H); MS (ESI+) m/z: 152 (M). 6a: 61.7% yield, mp 180.5-181.2℃; ¹H NMR (300 MHz, DMSO-d₆): δ 11.02 (br s, 1H), 7.50-7.59 (m, 1H), 7.48 (s, 1H), 7.05 (t, 1H, J = 6 Hz), 6.89 (d, 1H, J = 6 Hz). MS (ESI+) m/z: 170 (M+23). 6b: 34.6% yield, mp > 250℃; ¹H NMR (300 MHz, DMSO-d₆): δ 11.21 (br s, 1H), 7.55 (t, J = 6 Hz, 1H), 7.06 (d, J = 9 Hz, 1H), 6.86 (d, 1H, J = 3 Hz); MS (ESI+) m/z: 204 M + Na. 6c: 72.32% yield, mp > 250℃; ¹H NMR (300 MHz, DMSO-d₆): δ 11.13 (br s, 1H), 7.62 (dd, J = 6Hz, 3Hz, 1H), 7.56 (d, J = 3Hz, 1H), 6.92 (d, J = 9Hz, 1H); MS (ESI+) m/z: 204 [M + Na]⁺. 6d: 28.6% yield, mp > 250℃; ¹H NMR: (300 MHz, DMSO-d₆): δ 11.16 (br s, 1H), 7.53 (d, J = 6 Hz, 1H), 7.12 (dd, J = 6 Hz, 3 Hz, 1H), 6.94 (d, J = 3 Hz, 1H); MS (ESI+) m/z: 204 [M + Na]⁺. 6e: 66.5% yield, mp 180.6-181.8℃; ¹H NMR (300 MHz, DMSO-d₆): δ 11.46 (br s, 1H), 7.67 (d, J = 6Hz, 1H), 7.49 (d, J = 6 Hz, 1H), 7.09 (t, J = 6 Hz, 1H); MS (ESI+) m/z: 204 [M + Na]⁺. 6f: 38.1% yield, mp > 250℃; ¹H NMR (300 MHz, DMSO-d₆): δ 10.93 (s, 1H), 7.45 (t, J = 8.0 Hz, 1H), 7.22 (d, J = 8.1 Hz, 1H), 6.89 (d, J = 7.8 Hz, 1H). 6g: 67.2% yield, mp 250.5-251.3℃; ¹H NMR (300 MHz, DMSO-d₆): δ 11.16 (s, 1H), 7.73 (dd, J = 8.3, 2.1 Hz, 1H), 7.64 (d, J = 2.0 Hz, 1H), 6.88 (d, J = 8.3 Hz, 1H). 6h: 66.3% yield, mp 185.2-186.7℃; ¹H NMR (300 MHz, DMSO-d₆): δ 10.93 (s, 1H), 7.56-7.20 (m, 2H), 6.80 (d, J = 7.8 Hz, 1H). 6i: 25.7% yield, mp 201-201.2℃; ¹H NMR: (300 MHz, DMSO-d₆): δ 10.84 (s, 1H), 7.18 (dd, J = 8.5, 2.8 Hz, 1H), 7.07 (d, J = 2.7 Hz, 1H), 6.84 (d, J = 8.5 Hz, 1H). 6j: 77.5% yield, mp 131.6-132.3℃; ¹H NMR: (300 MHz, DMSO-d₆): δ 7.70 (t, 1H, J = 3Hz), 7.69 (dd, 1H, J = 6 Hz, 3 Hz), 7.17 (d, 2H, J = 6 Hz), 3.17 (s, 3H); MS (ESI+) m/z: 184 [M+Na]⁺. 6k: 81.2% yield, mp 129.4-130.3℃; ¹H NMR: (300 MHz, DMSO-d₆): δ 7.28-7.36 (m,7H), 7.12 (t, 1H, J = 3 Hz), 6.97 (d, 1H, J = 6 Hz), 4.91 (s, 2H); MS (ESI+) m/z: 260 [M + Na]⁺. 6l: 72.7% yield, mp 191.3-194.0℃; ¹H NMR (300 MHz, DMSO-d₆): δ 7.62(t, 1H, J = 3 Hz), 7.11 (t, 2H, J = 6 Hz), 3.14 (s, 3H); MS (ESI+) m/z: 218 [M + Na]⁺. 6m: 79.3% yield, mp 165.8-166.5℃; ¹H NMR (300 MHz, DMSO-d₆): δ 7.59(d, 1H, J = 3 Hz), 7.44 (d, 2H, J = 3 Hz),7.35 (t, 2H, J = 6 Hz), 7.30 (d, 1H, J = 3 Hz), 7.13-7.18 (m, 2H), 4.93 (s, 2H); MS (ESI+) m/z: 294[M + Na]⁺. 6n: 83.8% yield, mp 141.5-142.5℃; ¹H NMR (300 MHz, DMSO-d₆): δ 7.62 (t, 2H, J = 3 Hz), 7.43 (d, 2H, J = 6 Hz), 7.28-7.36 (m, 3H), 6.97 (d, 1H, J = 9 Hz), 4.91 (s, 2H); MS (ESI+) m/z: 294 [M + Na]⁺. 6o: 80.6% yield, mp 177.1-178.2℃; ¹H NMR (300 MHz, DMSO-d₆): δ 7.54 (d, 1H, J = 3 Hz), 7.33 (s, 1H), 7.16 (d, 2H, J = 3 Hz), 3.14 (s, 3H); MS (ESI+) m/z: 218 [M + Na]⁺. 6p: 85.1% yield, mp 175.2-176.1℃; ¹H NMR (300 MHz, DMSO-d₆): δ 7.53 (t, 1H, J = 6 Hz), 7.43 (d, 2H, J = 3 Hz), 7.28-7.36 (m, 3H), 7.11 (d, 1H, J = 3 Hz), 6.90 (d, 1H, J = 3 Hz), 4.91 (s, 2H); MS (ESI+) m/z: 294 [M + Na]⁺. 1a: yellow crystal; 39.3% yield, mp 208.8-210.8℃; 1HNMR(300 MHz, DMSO-d₆): δ 10.55 (s, 1H), 8.90 (s, 1H), 7.63-7.41 (m, 6H), 7.35-7.27 (m, 1H), 7.07 (t, 1H, J = 7.6 Hz), 6.88 (d, 1H, J = 7.8 Hz); MS (ESI+) m/z 304 [M + Na]⁺. 1b: orange crystal; 43.5% yield, mp 198.1-198.9℃; ¹H NMR: (300 MHz, DMSO-d₆) δ 10.84 (s, 1H), 8.71 (s, 1H), 7.55 (d, 2H, J = 6.0 Hz), 7.53-7.40 (m, 3H), 7.32 (t, 1H, J = 6.0 Hz), 7.07 (d, 1H, J = 9.0 Hz), 6.86 (d, 1H, J = 9.0 Hz); MS (ESI+) m/z: 338 [M + Na]⁺. 1c: light yellow crystal; 53.9% yield, mp 210.4-211.3℃; ¹H NMR (300MHz, DMSO-d₆): δ 10.66 (s, 1H), 8.90 (s, 1H), 7.62-7.31 (m, 7H), 6.88 (d, 1H, J = 8.3 Hz); MS (ESI+) m/z: 338 [M + Na]⁺. 1d: δ eep orange crystal; 52.5% yield, mp 213-214.2℃; ¹H NMR (300MHz, DMSO-d₆): δ 10.70 (s, 1H), 8.88 (s, 1H), 7.58-7.41 (m, 6H), 7.10 (dd, J = 8.0, 1.0 Hz, 1H), 6.89 (d, J = 1.0 Hz,1H);MS(ESI+) m/z 338 [M + Na]⁺. 1e: δ eep orange crystal; 61.0% yield, mp 213.2-214.2℃; ¹H NMR: (300 MHz, DMSO-d₆) δ 11.01 (s, 1H), 8.93 (s, 1H), 7.62-7.53 (m, 2H), 7.45 (dt, J = 18.2, 7.4 Hz, 5H), 7.09 (t,J = 7.8 Hz,1H);MS (ESI+) m/z 338 [M + Na]⁺. 1f: light yellow crystal; 39.5% yield, mp 195.8-196.5℃; ¹H NMR (300 MHz, DMSO-d₆): δ 10.82 (s, 1H), 8.70 (s, 1H), 7.58-7.52 (m, 2H), 7.49-7.39 (m, 3H), 7.26-7.20 (m, 2H), 6.89 (dd, 1H, J = 5.4, 3.0 Hz); MS (ESI+) m/z 383 [M + Na]⁺. 1g: scarlet crystal; 51.2% yield, mp 213.6-214.2℃; ¹H NMR: (300 MHz, DMSO-d₆) δ 10.69 (s, 1H), 8.91 (s, 1H), 7.63-7.39 (m, 7H), 6.84 (d, 1H, J = 8.3 Hz); MS (ESI+) m/z: 383 [M + Na]⁺. 1h: yellow crystal; 43.7% yield, mp 221.3-221.6℃; ¹H NMR: (300 MHz, DMSO-d₆) δ 10.31 (s, 1H), 7.90 (s, 1H), 7.68-7.61 (m, 2H), 7.46-7.33 (m, 3H), 7.08-6.98 (m, 2H), 6.75-6.68 (m, 1H), 2.22 (s, 3H); MS (ESI+) m/z: 318 [M + Na]⁺. 1i: green crystal; 62.3% yield, mp 189.4-189.8℃; ¹H NMR (300 MHz, DMSO-d₆): δ 10.34 (s, 1H), 8.88 (s, 1H), 7.59-7.50 (m, 2H), 7.45 (d, 3H, J = 7.1 Hz), 7.09 (d, 1H, J = 2.2 Hz), 6.89 (dd, 1H, J = 8.5, 2.8 Hz), 6.78 (d, 1H, J = 8.5 Hz), 3.72 (s, 3H); MS (ESI+) m/z: 334[M + Na]⁺. 1j: scarlet crystal; 33.6% yield, mp 207-208.1℃; ¹H NMR (300 MHz, DMSO-d₆): δ 8.84 (s, 1H), 7.71-7.27 (m, 8H), 7.24-6.94 (m, 2H), 3.14 (s, 3H); MS (ESI+) m/z 318 [M + Na]⁺. 1k: scarlet crystal; 57.2% yield, mp 156.7-157.2℃; ¹H NMR (300MHz, DMSO-d₆): δ 9.03 (s, 1H), 7.63-7.56 (m, 3H), 7.51-7.43 (m, 3H), 7.38-7.28 (m, 6H), 7.12 (t, 1H, J = 7.5 Hz), 6.93 (d, 1H, J = 7.8 Hz), 4.90 (s, 2H); MS (ESI+) m/z: 394 [M + Na]⁺. 1l: red crystal; 53.1% yield, mp 193.7-194.0℃; ¹H NMR (300MHz, DMSO-d₆): δ 8.69 (s, 1H), 7.59-7.51 (m, 2H), 7.50-7.36 (m, 5H), 7.11 (dd, 3H, J = 21.7, 8.1 Hz), 3.33 (s, 2H); MS (ESI+) m/z: 330 [M + H]⁺, 352 [M+Na]⁺. 1m: yellow crystal; 51.2% yield, mp 179.2-179.9℃; ¹H NMR (300MHz, DMSO-d₆): δ 8.87 (s, 1H), 7.65-7.27 (m, 11H), 7.05 (dd, 1H, J = 54.6, 8.0 Hz), 4.95 (dd, 2H, J = 32.1, 16.0 Hz);MS (ESI+) m/z: 406 [M + H]⁺, 428 [M+Na]⁺ . 1n: orange crystal; 55.7% yield, mp 141.5-142.5℃; ¹H NMR (300 MHz, DMSO-d₆): δ 9.06 (s, 1H), 7.59 (dd, 3H, J = 8.1, 1.6 Hz), 7.47 (dd, 3H, J = 7.1, 2.1 Hz), 7.44 7.34 (m, 5H), 6.97 (d, 1H, J = 7.8 Hz), 4.91 (d, 2H, J = 4.9 Hz); MS (ESI+) m/z: 406 [M + H]⁺, 428 [M + Na]⁺. 1o: red crystal; 49.3% yield, mp 177.1-178.2℃; ¹H NMR (300 MHz, DMSO-d₆): δ 8.83 (s, 1H), 7.61-7.52 (m, 3H), 7.51-7.42 (m, 3H), 7.25 (d, 1H, J = 2.0 Hz), 7.18 (dd, 1H, J = 7.9, 1.9 Hz), 3.15 (s, 3H); MS (ESI+) m/z: 330 [M + H]⁺, 352 [M+ Na]⁺. 1p: orange crystal; 47.6% yield, mp 175.2-176.1℃; ¹H NMR (300 MHz, DMSO-d₆): δ 9.02 (s, 1H), 7.66-7.54 (m, 4H), 7.51-7.42 (m, 4H), 7.40-7.28 (m, 7H), 7.19-7.14 (m, 1H), 7.10 (d, 1H, J = 1.7 Hz), 4.92 (d, 2H, J = 4.3 Hz);MS (ESI+) m/z 406[M + H]⁺, 428 [M+Na]⁺.
19. [19]
  [19] Z. Nikolovska-Coleska, R. Wang, X. Fang, et al., Development and optimization of a binding assay for the XIAP BIR3 domain using fluorescence polarization, Anal. Biochem. 332 (2004) e261-e273.
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