2-formylphenyl 4-nitrobenzenesulfonate | 116748-53-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-formylphenyl 4-nitrobenzenesulfonate
• 英文别名: (2-formylphenyl) 4-nitrobenzenesulfonate
• CAS: 116748-53-9
• 化学式: C₁₃H₉NO₆S
• 分子量: 307.284
• InChiKey: CSJAODIVMYAFOI-UHFFFAOYSA-N

物化性质

• 熔点：
  117-119 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  520.5±50.0 °C(Predicted)
• 密度：
  1.487±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-formylphenyl 4-nitrobenzenesulfonate 在 二叔丁基过氧化物 作用下， 以 氯苯 为溶剂， 反应 24.0h， 以52%的产率得到(2-hydroxyphenyl)(4-nitrophenyl)methanone
  参考文献：
  名称：

  一种通过分子内酰基自由基ipso取代制备2-羟基二芳基酮的简捷方法

  摘要：

  使用分子内酰基自由基[1,6] ipso取代反应可以简单地制备取代的2-羟基二芳基酮。

  DOI：

  10.1016/s0040-4039(00)01746-9
• 作为产物：
  描述：

  水杨醛 生成 2-formylphenyl 4-nitrobenzenesulfonate
  参考文献：
  名称：

  SANDERS, GEORGINE M.;VAN, DIJK MARINUS;VAN, VELDHUIZEN ALBERTUS;VAN, DER +, J. ORG. CHEM., 53,(1988) N 22, C. 5272-5281

  摘要：

  DOI：

文献信息

• New arylsulfonohydrazide inhibitors of enzymes MurC and MurD
  申请人：UNIVERZA V LJUBLJANI, FAKULTETA ZA FARMACIJO

  公开号：EP1845083A3

  公开（公告）日：2009-12-30

  This invention belongs to the field of pharmaceutical chemistry and relates to new arylsulfonohydrazides as inhibitors of UDP-N-acetylmuramyl:L-alanine ligaze (MurC) and UDP-N-acetylmuramyl-L-alanine:D-glutamate ligaze (MurD), to procedures for their preparation and pharmaceutical preparations containing the same. The enzymes MurC and MurD are the key enzymes involved in the synthesis of bacterial peptidoglycan, so arylsulfonohydrazide inhibitors possess antibacterial activity. Compounds of general formula I and the pharmaceutically acceptable salts are described. The appropriate substituents are clearly presented in the body of the text and in claims.

  这项发明属于药物化学领域，涉及新的芳基磺酰肼作为UDP-N-乙酰基葡萄糖胺基莫拉酰基:L-丙氨酸连接酶（MurC）和UDP-N-乙酰基葡萄糖胺基-L-丙氨酸:D-谷氨酸连接酶（MurD）的抑制剂，以及它们的制备方法和含有相同物质的药物制剂。酶MurC和MurD是参与细菌肽聚糖合成的关键酶，因此芳基磺酰肼抑制剂具有抗菌活性。描述了一般式I的化合物及其药用盐。适当的取代基在文本主体和权利要求中清晰呈现。
• Design and Synthesis of Novel N-Benzylidenesulfonohydrazide Inhibitors of MurC and MurD as Potential Antibacterial Agents
  作者：Rok Frlan、Andreja Kovač、Didier Blanot、Stanislav Gobec、Slavko Pečar、Aleš Obreza

  DOI：10.3390/molecules13010011

  日期：——

  A series of novel N-benzylidenesulfonohydrazide compounds were designedand synthesized as inhibitors of UDP-N-acetylmuramic acid:L-alanine ligase (MurC) andUDP-N-acetylmuramoyl-L-alanine:D-glutamate ligase (MurD) from E. coli, involved inthe biosynthesis of bacterial cell-walls. Some compounds possessed inhibitory activityagainst both enzymes with IC50 values as low as 30 μM. In addition, a new, one-potsynthesis of amidobenzaldehydes is reported.

  一系列新型N-苄叉磺酰肼化合物被设计并合成为大肠杆菌中UDP-N-乙酰胞壁酸:L-丙氨酸连接酶（MurC）和UDP-N-乙酰胞壁酰-L-丙氨酸:D-谷氨酸连接酶（MurD）的抑制剂，这两种酶参与细菌细胞壁的生物合成。部分化合物对这两种酶均显示出抑制活性，其IC50值低至30 μM。此外，还报道了一种新的亚胺基苯甲醛的一锅合成方法。
• Synthesis of 2-styryl-quinazoline and 3-styryl-quinoxaline based sulfonate esters <i>via</i> sp³ C–H activation and their evaluation for α-glucosidase inhibition
  作者：Neeli Satyanarayana、Boddu Ramya Sree、Kota Sathish、Sakkani Nagaraju、Kalivarathan Divakar、Ravinder Pawar、Thangellapally Shirisha、Dhurke Kashinath

  DOI：10.1039/d1nj05644a

  日期：——

  Synthesis of 2-styryl-quinazolines and 3-styryl-quinoxaline based sulfonates is reported via sp3 C–H functionalization in the presence of triethylamine (10 mol%). The resulting compounds were tested for α-glucosidase enzyme inhibition (in vitro) using acarbose as a standard drug (IC50 = 33 ± 2.65 μM) because α-glucosidases increase the carbohydrate digestion, and therefore the blood glucose levels

  报道了在三乙胺（10 mol%）存在下通过sp 3 C-H 官能化合成 2-苯乙烯基喹唑啉和 3-苯乙烯基喹喔啉基磺酸盐。使用阿卡波糖作为标准药物 (IC 50 = 33 ± 2.65 μM)测试所得化合物的 α-葡糖苷酶抑制（体外），因为 α-葡糖苷酶会增加碳水化合物的消化，因此会增加血糖水平。已知这种酶的抑制剂可以降低餐后高血糖。在筛选的化合物中，发现3o和5n具有活性，IC 50 = 28 ± 1.99 μM 和 IC 50= 32 ± 2.11 μM，分别具有竞争性抑制模式。使用 MAL12 同源模型的分子对接分析支持体外结果。使用DFT计算研究了5g的稳定性，发现顺式和反式(ΔE)异构体的总能量差为-85.67 kcal mol -1。
• METHOD FOR PRODUCING OPTICALLY ACTIVE CYANOHYDRIN COMPOUND
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP2264005A1

  公开（公告）日：2010-12-22

  A method of producing an optically active cyanohydrin compound represented by formula (3) (wherein, Q1 and Q2 are as defined below, and * represents that the indicated carbon atom is the optically active center) comprising reacting an aldehyde compound represented by formula (2) (wherein, Q1 and Q2 represent each independently a hydrogen atom, optionally substituted alkyl group having 1 to 6 carbon atoms, or the like) with hydrogen cyanide in the presence of a silyl compound and an asymmetric complex which is obtained by reacting an optically active pyridine compound represented by formula (1) (wherein, R1 and R2 represent each independently a hydrogen atom, alkyl group having 1 to 6 carbon atoms, or the like, provided that R1 and R2 are not the same.) with an aluminum halide.

  一种生产由式（3）表示的光学活性氰醇化合物的方法 (其中，Q1 和 Q2 如下文所定义，* 代表所指示的碳原子是光学活性中心）的方法，包括使式（2）所代表的醛化合物发生反应 (其中，Q1 和 Q2 各自独立地代表氢原子、具有 1 至 6 个碳原子的任选取代的烷基或类似基团）与氰化氢在硅烷基化合物和一种不对称络合物的存在下反应，该不对称络合物是由式（1）所代表的具有光学活性的吡啶化合物反应得到的 (其中，R1 和 R2 各自独立地代表氢原子、具有 1 至 6 个碳原子的烷基或类似基团，但 R1 和 R2 不能相同）与卤化铝反应。
• Synthesis and Antiproliferative Evaluation of 2′-Arenesulfonyloxy-5-benzylidene-thiazolidine-2,4-diones
  作者：Emily M. Chen、Pei-Jung Lu、Arthur Y. Shaw

  DOI：10.1002/jhet.859

  日期：2012.7

  A series of 2′‐arenesulfonyloxy‐5‐benzylidene‐thiazolidine‐2,4‐diones (TZDs) were synthesized and examined for their antiproliferative effects on a panel of carcinoma cell lines. Our results indicated that initial synthesis of 5‐[2′‐hydroxybenzylidene]‐2,4‐thiazolidinone (9) by Knoevenagel condensation followed by nucleophilic substitution with arylsulfonyl chlorides exhibited superior efficiency to the alternative synthetic route. Among tested compounds, only 8c and 8e showed significant antiproliferative activity against PC‐3 and BT474 cells with GI50 values of 8.4 and 20.6 μM, respectively. SKHep cells displayed interesting structure‐activity relationships in response to TZD derivatives treatment. Alkyl group‐substituted TZD analogs such as 8a (4‐Me, GI50, 9.4 μM) and 8k (4‐iso‐propyl, GI50, 9.8 μM) revealed better antiproliferative activity than those with bulkier alkyl groups. On the other hand, halogen‐substituted TZD analogs 8c, 8h, and 8i showed better antiproliferative activity against H460 cell line. Together, the new synthesized TZD derivatives 8a, 8b, 8c, 8d, 8e, 8f, 8g, 8h, 8i, 8j, 8k, 8l, 8m, 8n, 8o, 8p exhibited appreciable antiproliferative activity worth for further study.