4-((3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino)benzenesulfonamide | 6949-34-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-((3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino)benzenesulfonamide
• 英文别名: 4-[(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino]benzenesulfonamide；4-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-ylamino)benzenesulfonamide；N-(3-chloro-1,4-dioxo-1,4-dihydro-[2]naphthyl)-sulfanilic acid amide；N-(3-Chlor-1,4-dioxo-1,4-dihydro-[2]naphthyl)-sulfanilsaeure-amid；3--2-chlor-1.4-naphthochinon；4-[(3-Chloro-1,4-dioxonaphthalen-2-yl)amino]benzenesulfonamide
• CAS: 6949-34-4
• 化学式: C₁₆H₁₁ClN₂O₄S
• 分子量: 362.793
• InChiKey: ZCSWBRADQTXXKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  十八硫醇 、 4-((3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino)benzenesulfonamide 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以97%的产率得到4-((3-(octadecylthio)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino)benzenesulfonamide
  参考文献：
  名称：

  用于检测Hg 2+离子的双通道比色和比例荧光化学传感器及其生物成像应用

  摘要：

  合成了一种新的比色和比例荧光化学传感器4-（（3-（十八烷基硫基）-1,4-二氧代-1,4-二氢萘-2-基）氨基）苯磺酰胺（4DBS），并进行了选择性检测Hg 2的研究。 +在DMSO-H 2 O（9：1，v / v）溶液中。化学传感器通过迈克尔样加成和亲核取代反应分两步有效合成。获得了相对于Hg 2+的比例荧光开启响应，并且由于分子内电荷转移效应，其荧光发射峰红移了140 nm，并伴随着从浅褐红色到淡黄色的颜色变化。FT-IR进一步评估了形成的配位金属络合物11 H NMR和量子化学分析证实结合机理。检测过程是敏感/可逆的，计算出的Hg 2+的检出限为0.451 µM。此外，4DBS被有效地利用作为生物成像剂检测汞2+在活细胞和斑马鱼幼体。另外，与正常细胞相比，4DBS在癌细胞中显示出对Hg 2+的区别检测。因此，4DBS可以用作区分人癌细胞的有效生物成像探针。

  DOI：

  10.1016/j.saa.2021.119776
• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 、 磺胺 以 水 为溶剂， 反应 3.0h， 以98%的产率得到4-((3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino)benzenesulfonamide
  参考文献：
  名称：

  用于溶液中Sn 2+离子选择性检测的简单比色和荧光化学传感探针：新型传感机制及其生物成像应用的评估

  摘要：

  成功开发出一种易于使用的比色和荧光探针4-（（3-氯-1,4-二氧杂-1,4-二氢萘-2-基）氨基）苯磺酰胺（4CBS）用于选择性和灵敏地检测Sn 2+在水溶液中。传感机制涉及在添加Sn 2+时，将4 CBS中的-C═O还原为-C-OH基团，从而启动荧光开启模式。荧光强度和Sn 2+浓度在0-62.5μM范围内具有更好的线性关系，检出限（LOD）为0.115μM。4CBS与Sn 2+的结合机理通过傅立叶变换红外分析，NMR滴定和质谱（电喷雾电离）光谱分析得到证实。同样，拟议的传感机制得到了量子化学计算的支持。此外，生物成像研究表明，化学传感探针4CBS是检测活细胞和斑马鱼中Sn 2+的有效荧光标记。显著，4CBS能够锡区分2+在人类癌细胞和Sn 2+在正常活细胞。

  DOI：

  10.1021/acs.analchem.0c03196

文献信息

• Synthesis and<i>In Vitro</i>Biological Evaluation of Aminonaphthoquinones and Benzo[<i>b</i>]phenazine-6,11-dione Derivatives as Potential Antibacterial and Antifungal Compounds
  作者：Amaç Fatih Tuyun、Nilüfer Bayrak、Hatice Yıldırım、Nihal Onul、Emel Mataraci Kara、Berna Ozbek Celik

  DOI：10.1155/2015/645902

  日期：——

  A series of 2-arylamino-3-chloro-1,4-naphthoquinone derivatives (3a–h) by the reaction of 2,3-dichloro-1,4-naphthoquinone with aryl amines (2a–h) and benzo[b]phenazine-6,11-dione derivatives (4a–c) by the treatment of 2-arylamino-3-chloro-1,4-naphthoquinone derivatives (3a–h) with sodium azide were synthesized and tested for theirin vitroantibacterial and antifungal activities. The results suggest that compounds3dand3ghad potent antifungal activity againstCandida albicans(MIC = 78.12 μg/mL). All synthesized compounds (3a–h,4a–c) possessed activity againstE. faecaliswith MIC values of between 312.5 and 1250 μg/mL. Benzo[b]phenazine-6,11-dione derivatives (4a–c) were mostly active against Gram-positive bacteria. The structures of the new members of the series were established on the basis of their spectral properties (IR,¹H NMR,¹³C NMR, and mass spectrometry).

  一系列2-芳胺基-3-氯-1,4-萘醌衍生物（3a-h）通过2,3-二氯-1,4-萘醌与芳胺基（2a-h）和苯并[b]苝啉-6,11-二酮衍生物（4a-c）反应合成，方法是将2-芳胺基-3-氯-1,4-萘醌衍生物（3a-h）与叠氮化钠处理后进行检测其体外抗菌和抗真菌活性。结果表明，化合物3d和3g对白念珠菌（MIC = 78.12 μg/mL）具有强效的抗真菌活性。所有合成的化合物（3a-h，4a-c）对肠球菌具有活性，MIC值在312.5和1250 μg/mL之间。苯并[b]苝啉-6,11-二酮衍生物（4a-c）主要对革兰氏阳性细菌活性较强。这一系列新成员的结构是基于它们的光谱特性（红外光谱，1H核磁共振，13C核磁共振和质谱）确定的。
• PROTEASOME INHIBITORS FOR SELECTIVELY INDUCING APOPTOSIS IN CANCER CELLS
  申请人：Lawrence Harshani

  公开号：US20110201609A1

  公开（公告）日：2011-08-18

  The subject invention concerns compounds having activity as inhibitors of proteasomes and methods of using the subject compounds. In one embodiment, a compound of the invention has the chemical structure shown in formula I: wherein R 1 is an organic cyclic ring structure bonded to a sulfonamide structure; R 2 is H, halogen, alkyl, —NR 6 R 7 , or heteroalkyl; R 3 is H, halogen, —OH, —O-alkyl, alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, —NO 2 , —NH 2 or substituted amines; R 4 is H, alkyl, heteroalkyl, aryl, or heteroaryl, any of which can be optionally substituted with one or more of —NO 2 , alkyl, heteroalkyl, aryl, or heteroaryl, or halogen; R 5 is H, —OH, halogen, alkyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, —O-alkyl, —O-aryl, heteroalkyl, —NO 2 , —NH 2 , or substituted amine; and R 6 and R 7 are independently H, O, alkyl, aryl, heterocycloalkyl, or heteroaryl, or together can form a heterocycloalkyl or a heteroaryl, any of which can be optionally substituted with one or more of —NO 2 , alkyl, heteroalkyl, aryl, or halogen; or a pharmaceutically acceptable salt or hydrate thereof. In another embodiment, a compound of the invention has the chemical structure shown in formula II: wherein Q, W, X, Y, Z are each independently carbon, oxygen, or nitrogen; R 1 is H, or X 1 R 8 ; R 2 is heteroalkyl, which can be optionally substituted with one or more of —OH, halogen, —C(O)OR 4 , alkyl, heteroalkyl, heterocycloalkyl, or heteroaryl; R 3 is heterocycloalkyl, aryl, heteroaryl, any of which can be optionally substituted with one or more of a halogen or —OH; and R 4 is H or alkyl; R 5 is halogen, alkyl or nitro; R 6 is nitro, X 2 R 9 or a halogen; R 7 is H or alkyl; R 8 is H, alkyl, aryl, CH 2 -alkyl-aryl, -alkyl-C(O)OH, or alkyl-tetrazole (aromatic and aliphatic heterocyclic groups); R 9 is H or alkyl; X 1 is oxygen, nitrogen, or sulfur; X 2 is oxygen, nitrogen, or sulfur; or a pharmaceutically acceptable salt or hydrate thereof.

  本发明涉及作为蛋白酶体抑制剂的化合物及使用该化合物的方法。在一种实施方式中，本发明的化合物具有公式I所示的化学结构：其中，R1是与磺酰胺结构键合的有机环状环结构；R2是H、卤素、烷基、-NR6R7或杂环烷基；R3是H、卤素、-OH、-O-烷基、烷基、环烷基、杂环烷基、芳基、杂芳基、-NO2、-NH2或取代胺；R4是H、烷基、杂烷基、芳基或杂芳基，其中任何一个都可以选择性地取代一个或多个-NO2、烷基、杂烷基、芳基或杂芳基或卤素；R5是H、-OH、卤素、烷基、芳基、杂芳基、环烷基、杂环烷基、-O-烷基、-O-芳基、杂烷基、-NO2、-NH2或取代胺；R6和R7分别是H、O、烷基、芳基、杂环烷基或杂芳基，或者一起形成杂环烷基或杂芳基，其中任何一个都可以选择性地取代一个或多个-NO2、烷基、杂烷基、芳基或卤素；或其药学上可接受的盐或水合物。在另一种实施方式中，本发明的化合物具有公式II所示的化学结构：其中，Q、W、X、Y、Z分别独立地是碳、氧或氮；R1是H或X1R8；R2是杂环烷基，可以选择性地取代一个或多个-OH、卤素、-C（O）OR4、烷基、杂烷基、杂环烷基或杂芳基；R3是杂环烷基、芳基、杂芳基，其中任何一个都可以选择性地取代一个或多个卤素或-OH；R4是H或烷基；R5是卤素、烷基或硝基；R6是硝基、X2R9或卤素；R7是H或烷基；R8是H、烷基、芳基、CH2-烷基-芳基、-烷基-C（O）OH或烷基-四唑（芳香和脂肪族杂环基）；R9是H或烷基；X1是氧、氮或硫；X2是氧、氮或硫；或其药学上可接受的盐或水合物。
• Alcalay, 1947, vol. 10, p. 229,241
  作者：Alcalay

  DOI：——

  日期：——
• Buu-Hoi, Bulletin de la Societe Chimique de France, 1944, vol. <5> 11, p. 578,581
  作者：Buu-Hoi

  DOI：——

  日期：——
• Synthesis and biological evaluation of naphthoquinone analogs as a novel class of proteasome inhibitors
  作者：Harshani R. Lawrence、Aslamuzzaman Kazi、Yunting Luo、Robert Kendig、Yiyu Ge、Sanjula Jain、Kenyon Daniel、Daniel Santiago、Wayne C. Guida、Saïd M. Sebti

  DOI：10.1016/j.bmc.2010.06.038

  日期：2010.8

  Screening of the NCI Diversity Set-1 identified PI-083 (NSC-45382) a proteasome inhibitor selective for cancer over normal cells. Focused libraries of novel compounds based on PI-083 chloronaphthoquinone and sulfonamide moieties were synthesized to gain a better understanding of the structure-activity relationship responsible for chymotrypsin-like proteasome inhibitory activity. This led to the demonstration that the chloronaphthoquinone and the sulfonamide moieties are critical for inhibitory activity. The pyridyl group in PI-083 can be replaced with other heterocyclic groups without significant loss of activity. Molecular modeling studies were also performed to explore the detailed interactions of PI-083 and its derivatives with the beta 5 and beta 6 subunits of the 20S proteasome. The refined model showed an H-bond interaction between the Asp-114 and the sulfonamide moiety of the PI-083 in the beta 6 subunit. (C) 2010 Elsevier Ltd. All rights reserved.