6-chloronicotinoyl isothiocyanate | 851052-25-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-chloronicotinoyl isothiocyanate
• 英文别名: 6-Chloropyridine-3-carbonyl isothiocyanate；6-chloropyridine-3-carbonyl isothiocyanate
• CAS: 851052-25-0
• 化学式: C₇H₃ClN₂OS
• 分子量: 198.633
• InChiKey: IQDUOZXYTQNMES-UHFFFAOYSA-N

物化性质

• 沸点：
  331.9±27.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-chloronicotinoyl isothiocyanate 在 溴 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 1.75h， 生成 6-Chloro-N-(5-chloro-7-methoxy-[1,2,4]thiadiazolo[2,3-a]pyrimidin-2-ylidene)-nicotinamide
  参考文献：
  名称：

  Xue, Sijia; Ke, Shaoyong; Duan, Liping, Journal of the Indian Chemical Society, 2005, vol. 82, # 1, p. 79 - 82

  摘要：

  DOI：
• 作为产物：
  描述：

  6-氯烟酸 在 氯化亚砜 作用下， 以 PEG-400 、 甲苯 、 乙腈 为溶剂， 反应 2.5h， 生成 6-chloronicotinoyl isothiocyanate
  参考文献：
  名称：

  带有嘧啶部分的取代烟碱基硫脲衍生物：合成与生物学评价

  摘要：

  在超声辐射下，使用PEG-400作为固液相转移催化剂，合成了一系列含有嘧啶环的取代烟酰胺基硫脲衍生物，收率良好。通过IR，1 H NMR和元素分析阐明并确认了所有新合成的化合物的结构。初步的生物学测试表明，某些目标化合物对双子叶植物的根和茎具有良好的抑制活性，对单子叶植物是安全的。

  DOI：

  10.1007/s11164-010-0235-1

文献信息

• Aroylguanidine-based factor Xa inhibitors: The discovery of BMS-344577
  作者：Yan Shi、Chi Li、Stephen P. O’Connor、Jing Zhang、Mengxiao Shi、Sharon N. Bisaha、Ying Wang、Doree Sitkoff、Andrew T. Pudzianowski、Christine Huang、Herbert E. Klei、Kevin Kish、Joseph Yanchunas、Eddie C.-K. Liu、Karen S. Hartl、Steve M. Seiler、Thomas E. Steinbacher、William A. Schumacher、Karnail S. Atwal、Philip D. Stein

  DOI：10.1016/j.bmcl.2009.10.084

  日期：2009.12

  We report the design and synthesis of a novel class of N,N′-disubstituted aroylguanidine-based lactam derivatives as potent and orally active FXa inhibitors. The structure–activity relationships (SAR) investigation led to the discovery of the nicotinoyl guanidine 22 as a potent FXa inhibitor (FXa IC50 = 4 nM, EC2×PT = 7 μM). However, the potent CYP3A4 inhibition activity (IC50 = 0.3 μM) of 22 precluded

  我们报告设计和合成的新型的N，N'-二取代的芳基胍基内酰胺衍生物作为有效和口服活性FXa抑制剂。通过结构-活性关系（SAR）研究，发现了烟酰胍22作为有效的FXa抑制剂（FXa IC 50  = 4 nM，EC 2×PT  = 7μM）。然而，有效的CYP3A4抑制活性（IC 50  = 0.3μM）的22排除其进一步发展。对与FXa结合的化合物22的X射线晶体结构的详细分析表明，取代基位于22的烟酰基基团的6位上会暴露在溶剂中，这表明减弱不需要的CYP活性的努力可以集中在这个位置上，而不会显着影响FXa的效力。对6-取代的烟酰胺基胍进行的进一步SAR研究导致发现了6-（二甲基氨基甲酰基）烟酰胍36（BMS-344577，IC 50  = 9 nM，EC 2×PT  = 2.5μM），发现具有选择性，口服有效的FXa抑制剂，在动物模型中具有出色的体外耐受性，良好的药代动力学和药效学。
• Synthesis, cytotoxic, antibacterial, antioxidant activities, DFT, and docking of novel complexes of Palladium (II) containing a thiourea derivative and diphosphines
  作者：Rahman Azeez Muhammed、Bayazeed Hassan Abdullah、Heshu Sulaiman Rahman

  DOI：10.1016/j.molstruc.2023.136519

  日期：2024.1

  A thiourea ligand; N, N-di-(4-tolyl)-N'-(6-chloronicotinoyl) thiourea (LH) was synthesized from the reaction of 6-chloronicotinyl chloride with potassium thiocyanate which gave 6-chloronicotinoyl isothiocyanate, then reaction of 6–chloronicotinoyl isothiocyanate with Di-p-tolylamine in acidic medium gave the desired ligand (LH). Treatment of LH with K2PdCl4 gave a complex of [Pd(L)2]1. Reaction of

  硫脲配体；N,N-二-(4-甲苯基)-N'-(6-氯烟酰)硫脲(LH)由6-氯烟酰氯与硫氰酸钾反应生成6-氯烟酰异硫氰酸酯，然后与6-氯烟酰反应合成N,N-二-(4-甲苯基)-N'-(6-氯烟酰)硫脲(LH)。异硫氰酸酯与二对甲苯胺在酸性介质中得到所需的配体(LH)。用K 2 PdCl 4处理LH得到[Pd(L) 2 ]1络合物。络合物 1 与 Ph 2 P(CH 2 ) 2 PPh 2 (dppe) 和 Ph 2 P(CH 2 ) 3 PPh 2 (dppp) 中的每一个反应产生 [Pd(II)(L) 2 (Ph 2分别为P(CH 2 ) 2 PPh 2 )] 2 和[Pd(II)(L) 2 (Ph 2 P(CH 2 ) 3 PPh 2 )] 3 。用一些过渡金属处理配合物 2 和 3 得到异质双核配合物 [(Ph 2 P(CH 2 ) 2 PPh 2 ) Pd(II)(μ-L) 2 MCl
• Quinoxalin-2(1<i>H</i>)-One Derivatives As Inhibitors Against Hepatitis C Virus
  作者：Rui Liu、Zhuhui Huang、Michael G. Murray、Xiaoyong Guo、Gang Liu

  DOI：10.1021/jm200394x

  日期：2011.8.25

  Hepatitis C virus (HCV) infection is a serious problem worldwide, but no effective drugs are currently available. Through screening of our privileged structure library, quinoxalin-2(1H)-one derivative N-(7-(cyclohexyl(methyl)amino)-3-oxo-3,4-dihydroquinoxalin-6-ylcarbamothioyl)benzamide (compound 1) was identified as potent HCV inhibitor in vitro. Subsequently, a structure-activity relationship analysis was carried out that showed N-(7-(cyclohexyl(methyl)amino)-3-oxo-3,4-dihydroquinoxalin-6-ylcarbamothioyl)-furan-2-carboxamide (compound 11, EC(50) = 1.8 mu M, SI = 9.6), 6-(cyclohexyl-(methyl)amino)-7-(4-phenylthiazol-2-ylamino)quinoxalin-2(1H)-one (compound 33, EC(50) = 1.67 mu M, SI = 37.4), 2-(cyclohexyl(methyl)amino)-3-(4-phenylthiazol-2-ylamino)-7,8,9,10-tetrahydro-5H-pyrido[1,2-a]quinoxalin-6(6aH)-one (compound 60, EC(50) = 1.19 mu M, SI = 9.27), 8-(cyclohexyl(methyl)amino)-7-(4-phenylthiazol-2-ylamino)pyrrolo[1,2-a] quinoxalin-4(5H)-one (compound 65, EC(50) = 1.82 mu m, SI = 9.9), and 6-(diethylamino)-7-(4-phenylthiazol-2-ylamino)quinoxalin-2(1H)-one (compound 78, EC(50) = 1.27 mu M, SI = 17.9) acted against HCV. The data from the structure activity relationship study suggests that quinoxalin-2(1H)-one derivatives exhibited potent activity against HCV.
• Design, synthesis and potent cytotoxic activity of novel podophyllotoxin derivatives
  作者：Wen-Qun Li、Xu-Li Wang、Keduo Qian、Ying-Qian Liu、Chih-Ya Wang、Liu Yang、Jin Tian、Susan L. Morris-Natschke、Xing-Wen Zhou、Kuo-Hsiung Lee

  DOI：10.1016/j.bmc.2013.01.069

  日期：2013.4

  Twenty new acyl thiourea derivatives of podophyllotoxin and 4'-demethylepipodophyllotoxin were prepared and screened for their cytotoxicity against four human tumor cell lines, A-549, DU-145, KB, and KBvin. With IC50 values of 0.098-1.13 mu M, compounds 13b, 13c, and 13o displayed much better cytotoxic activity than the control etoposide. Most importantly, 13b and 13o exhibited promising cytotoxicity against the drug resistant tumor cell line KBvin with IC50 values of 0.098 and 0.13 mu M, respectively, while etoposide lost activity completely. Structure-activity relationship (SAR) correlations of the new derivatives have been established. Compounds 13b and 13o merit further development as a new generation of epipodophyllotoxin-derived antitumor clinical trial candidates. (C) 2013 Elsevier Ltd. All rights reserved.
• Substituted-nicotinyl thiourea derivatives bearing pyrimidine moiety: synthesis and biological evaluation
  作者：Shaoyong Ke、Xiufang Cao

  DOI：10.1007/s11164-010-0235-1

  日期：2011.7

  A series of substituted-nicotinyl thiourea derivatives containing pyrimidine ring were synthesized in good to excellent yield using PEG-400 as solid–liquid phase transfer catalyst under ultrasonic irradiation. The structures of all newly synthesized compounds were elucidated and confirmed by IR, 1H NMR and elemental analysis. The preliminary biological tests show that some of the target compounds present

  在超声辐射下，使用PEG-400作为固液相转移催化剂，合成了一系列含有嘧啶环的取代烟酰胺基硫脲衍生物，收率良好。通过IR，1 H NMR和元素分析阐明并确认了所有新合成的化合物的结构。初步的生物学测试表明，某些目标化合物对双子叶植物的根和茎具有良好的抑制活性，对单子叶植物是安全的。