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1 Supporting Information A new series of cytotoxic pyrazoline derivatives as potential anticancer agents induces cell cycle arrest and apoptosis Hong Wang 1,, Jinhong Zheng 1,, Weijie Xu 1, Cheng Chen 1, Duncan Wei 2, Wenxiu Ni 1, * and Ying Pan 1, * 1 Department of Chemistry, Shantou University Medical College, Shantou , Guangdong, China; @163.com (H.W.); jhzheng@stu.edu.cn (J.Z.); @163.com (W.X.); @163.com (C.C.) 2 Department of pharmacy, The First Affiliated Hospital of Shantou University Medical College, Shantou , Guangdong, China; weiduncan2012@163.com * Correspondence: wxni@stu.edu.cn; ypan@stu.edu.cn; Tel.: ; Fax: These authors contributed equally to this work. Contents Figure S1. The representative 1 H NMR of all compounds 1b-12b. 1 H NMR spectrum of compounds 1b-12b (400 MHz, DMSO) 1b
2 2b
3
4 3b
5 4b
6
7 5b
8 6b
9
10 7b
11 8b
12
13 9b
14 10b
15
16 11b
17 12b
18
19 Figure S2. The representative 13 C NMR of compound 1b and compound 2b. 13 C NMR spectrum of compound 1b and 2b (150 MHz, DMSO) 1b
20 2b 3b 4b
21 5b
22 7b 8b 9b
23 10b 11b
24 12b Figure S3. The representative HRMS (ESI) spectra of compound 1b-12b.
25 Relative Abundance HRMS (ESI) spectrum of compound 1b _ #9 RT: 0.09 AV: 1 NL: 3.43E7 T: FTMS + p ESI Full ms [ ] F OCH 3 70 N N OCH 3 60 S NH 2 OCH m/z Elemental Composition calculator Target M/Z Result type: Positive Species: [M+H] + Elements: C(0-40); H(0-80); O(0-10); N(0-10); F(0-1); S(0-1) Ion Formula Calculated M/Z PPM error C 19 H 21 N 3 O 3 FS HRMS (ESI) spectrum of compound 2b
26 Relative Abundance Relative Abundance _ #11 RT: 0.10 AV: 1 NL: 8.29E7 T: FTMS + p ESI Full ms [ ] Cl OCH N N OCH 3 60 S NH 2 OCH m/z Elemental Composition calculator Target M/Z Result type: Positive Species: [M+H] + Elements: C(0-40); H(0-80); O(0-10); N(0-10); Cl(0-1); S(0-1) Ion Formula Calculated M/Z PPM error C 19 H 21 N 3 O 3 SCl HRMS (ESI) spectrum of compound 3b Mazhengyue-b3 #15 RT: 0.15 AV: 1 NL: 9.17E7 T: FTMS + p ESI Full ms [ ] m/z
27 Relative Abundance Elemental Composition calculator Target M/Z Result type: Positive Species: [M+H] + Elements: C(0-40); H(0-80); O(0-10); N(0-10); Br(0-1); S(0-1) Ion Formula Calculated M/Z PPM error C 19 H 20 BrN 3 O 3 S HRMS (ESI) spectrum of compound 4b Mazhengyue-b4 #11 RT: 0.11 AV: 1 NL: 1.44E9 T: FTMS + p ESI Full ms [ ] m/z Elemental Composition calculator Target M/Z Result type: Positive Species: [M+Na] + Elements: C(0-40); H(0-80); O(0-10); N(0-10); S(0-1) Ion Formula Calculated M/Z PPM error C 20 H 23 N 3 O 3 S HRMS (ESI) spectrum of compound 5b
28 Relative Abundance Relative Abundance Mazhengyue-b5 #11 RT: 0.11 AV: 1 NL: 1.05E8 T: FTMS + p ESI Full ms [ ] m/z Elemental Composition calculator Target M/Z Result type: Positive Species: [M+Na] + Elements: C(0-40); H(0-80); O(0-10); N(0-10); Br(0-1); Cl(0-1); S(0-1) Ion Formula Calculated M/Z PPM error C 17 H 15 BrClN 3 O 2 S HRMS (ESI) spectrum of compound 6b Mazhengyue-b6 #13 RT: 0.13 AV: 1 NL: 2.33E8 T: FTMS + p ESI Full ms [ ] m/z Elemental Composition calculator
29 Relative Abundance Target M/Z Result type: Positive Species: [M+Na] + Elements: C(0-40); H(0-80); O(0-10); N(0-10); Br(0-1); S(0-1) Ion Formula Calculated M/Z PPM error C 17 H 15 Br 2 N 3 O 2 S HRMS (ESI) spectrum of compound 7b Mazhengyue-b7 #11 RT: 0.11 AV: 1 NL: 5.37E8 T: FTMS + p ESI Full ms [ ] m/z Elemental Composition calculator Target M/Z Result type: Positive Species: [M+Na] + Elements: C(0-40); H(0-80); O(0-10); N(0-10); Br(0-1); S(0-1) Ion Formula Calculated M/Z PPM error C 17 H 16 BrN 3 O 3 S HRMS (ESI) spectrum of compound 8b
30 Relative Abundance Relative Abundance Mazhengyue-b8 #11 RT: 0.11 AV: 1 NL: 1.42E9 T: FTMS + p ESI Full ms [ ] m/z Elemental Composition calculator Target M/Z Result type: Positive Species: [M+Na] + Elements: C(0-40); H(0-80); O(0-10); N(0-10); S(0-1) Ion Formula Calculated M/Z PPM error C 18 H 19 N 3 O 4 S HRMS (ESI) spectrum of compound 9b Mazhengyue-b9 #11 RT: 0.11 AV: 1 NL: 4.97E8 T: FTMS + p ESI Full ms [ ] m/z Elemental Composition calculator
31 Relative Abundance Target M/Z Result type: Positive Species: [M+Na] + Elements: C(0-40); H(0-80); O(0-10); N(0-10); Br(0-1); S(0-1) Ion Formula Calculated M/Z PPM error C 18 H 18 BrN 3 O 3 S HRMS (ESI) spectrum of compound 10b Mazhengyue-b10 #11 RT: 0.11 AV: 1 NL: 1.36E9 T: FTMS + p ESI Full ms [ ] m/z Elemental Composition calculator Target M/Z Result type: Positive Species: [M+Na] + Elements: C(0-40); H(0-80); O(0-10); N(0-10); S(0-1) Ion Formula Calculated M/Z PPM error C 19 H 21 N 3 O 4 S HRMS (ESI) spectrum of compound 11b
32 Relative Abundance Relative Abundance Mazhengyue-b11 #13 RT: 0.13 AV: 1 NL: 1.64E9 T: FTMS + p ESI Full ms [ ] m/z Elemental Composition calculator Target M/Z Result type: Positive Species: [M+Na] + Elements: C(0-40); H(0-80); O(0-10); N(0-10); S(0-1) Ion Formula Calculated M/Z PPM error C 20 H 23 N 3 O 4 S HRMS (ESI) spectrum of compound 12b Mazhengyue-b12 #11 RT: 0.11 AV: 1 NL: 4.58E8 T: FTMS + p ESI Full ms [ ] m/z Elemental Composition calculator
33 Target M/Z Result type: Positive Species: [M+Na] + Elements: C(0-40); H(0-80); O(0-10); N(0-10); Br(0-1); S(0-1) Ion Formula Calculated M/Z PPM error C 18 H 18 BrN 3 O 2 S Figure S4. The representative IR of compound 1b-12b. 1b 2b 3b
34 4b 5b 6b
35 7b 8b 9b
36 10b 11b 12b
37 Figure S5. The representative HPLC chromatogram of compound 1b-12b. Purity determination of compound 1b RT Area Height Peak Symmetry %Area width factor Purity determination of compound 2b
38 RT Area Height Peak Symmetry %Area width factor Purity determination of compound 3b RT Area Height Peak Symmetry %Area width factor Purity determination of compound 4b
39 RT Area Height Peak Symmetry %Area width factor Purity determination of compound 5b RT Area Height Peak Symmetry %Area width factor E Purity determination of compound 6b
40 RT Area Height Peak Symmetry %Area width factor Purity determination of compound 7b RT Area Height Peak Symmetry %Area width factor Purity determination of compound 8b RT Area Height Peak Symmetry %Area width factor Purity determination of compound 9b
41 RT Area Height Peak Symmetry %Area width factor Purity determination of compound 10b RT Area Height Peak Symmetry %Area width factor Purity determination of compound 11b RT Area Height Peak width Symmetry factor %Area
42 Purity determination of compound 12b RT Area Height Peak Symmetry %Area width factor
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