toluene-4-thiosulfonic acid S-propyl ester | 90494-81-8

• 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: toluene-4-thiosulfonic acid S-propyl ester
• 英文别名: S-propyl p-toluenethiosulfonate；1-methyl-4-propylsulfanylsulfonylbenzene
• CAS: 90494-81-8
• 化学式: C₁₀H₁₄O₂S₂
• 分子量: 230.352
• InChiKey: OCHCAHLZUFAELQ-UHFFFAOYSA-N

物化性质

• 沸点：
  115-116 °C(Press: 1-2 Torr)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  toluene-4-thiosulfonic acid S-propyl ester 、 potassium thioacetate 以 二氯甲烷 为溶剂， 生成 Acetyl-aethyldisulfid
  参考文献：
  名称：

  Unsymmetrical Organotrisulfide Formation via Low-Temperature Disulfanyl Anion Transfer to an Organothiosulfonate

  摘要：

  New methodology is presented for the formation of unsymmetrical organotrisulfides in a high yield and purity, relatively free of polysulfide byproducts. The highlight of the method is the low-temperature (-78 degrees C) deprotection of a disulfanyl acetate with sodium methoxide in THF to form a disulfanyl anion, which reacts rapidly in situ with an organothiosulfonate (S-aryl or S-alkyl) within 30 seconds followed by quenching. The discovery of these new reaction conditions together with the relative greenness of the chemistry overall makes for an efficient protocol, from which a range of organotrisulfides covering aliphatic, aromatic, as well as cysteine and sugar groups can be accessed in a high yield and purity.

  DOI：

  10.1021/acs.joc.8b03262
• 作为产物：
  描述：

  sodium 4-methylbenzenesulfonothioate 生成 toluene-4-thiosulfonic acid S-propyl ester
  参考文献：
  名称：

  GOODRIDGE, RICHARD J.;HAMBLEY, TREVOR W.;HAYNES, RICHARD K.;RIDLEY, DAMON+, J. ORG. CHEM., 53,(1988) N 13, 2881-2889

  摘要：

  DOI：

文献信息

• The cytotoxicity of garlic-related disulphides and thiosulfonates in WHCO1 oesophageal cancer cells is dependent on S-thiolation and not production of ROS
  作者：Muneerah Smith、Roger Hunter、Nashia Stellenboom、Daniel A. Kusza、M. Iqbal Parker、Ahmed N.H. Hammouda、Graham Jackson、Catherine H. Kaschula

  DOI：10.1016/j.bbagen.2016.03.032

  日期：2016.7

  mechanism that relies on the thermodynamics of a mixed disulphide exchange reaction. Disulphide (1) and thiosulfonate (11) were further evaluated mechanistically and found to induce G2/M cell-cycle arrest and apoptosis, inhibit cell proliferation, and generate ROS. When the ROS produced by 1 and 11 were quenched with Trolox, ascorbic acid or N-acetyl cysteine (NAC), only NAC was found to counter the cytotoxicity

  背景 大蒜因其促进健康和预防癌症的特性已在民间医学中使用了多个世纪。压碎的大蒜中的生物活性成分是烯丙基硫化合物，被提议通过（i）蛋白S-硫醇化和（ii）产生ROS进行化学反应。 方法 合成了一组R-丙基二硫化物和R-硫代磺酸盐化合物，以探讨硫解和ROS生成在WHCO1食管癌细胞中大蒜相关化合物的细胞毒性中的重要性。 结果  发现细胞毒性IC 50与R-丙基二硫化物和硫代磺酸盐的离去基团pK a之间存在显着的相关性（R 2 = 0.78，Fcrit（7,1）α= 0.005），支持了依赖于C混合二硫化物交换反应。对二硫化物（1）和硫代磺酸盐（11）进行了进一步的机械评估，发现它们可诱导G 2 / M细胞周期停滞和凋亡，抑制细胞增殖并产生ROS。当用Trolox，抗坏血酸或N淬灭1和11产生的ROS时-乙酰半胱氨酸（NAC），只有NAC被发现可以抵消两种化合物的细胞毒性。但是，发现NAC通过混
• Structure–activity studies on the anti-proliferation activity of ajoene analogues in WHCO1 oesophageal cancer cells
  作者：Catherine H. Kaschula、Roger Hunter、Nashia Stellenboom、Mino R. Caira、Susan Winks、Thozama Ogunleye、Philip Richards、Jonathan Cotton、Kani Zilbeyaz、Yabing Wang、Vuyolwethu Siyo、Ellen Ngarande、M. Iqbal Parker

  DOI：10.1016/j.ejmech.2012.01.058

  日期：2012.4

  organosulfur compound ajoene derived from the rearrangement of allicin found in crushed garlic can inhibit the proliferation of tumour cells by inducing G2/M cell cycle arrest and apoptosis. We report on the application of a concise four-step synthesis (Hunter et al., 2008 [1]) that allows access to ajoene analogues with the end allyl groups substituted. A library of twelve such derivatives tested for

  大蒜碎物中发现的大蒜素重排产生的有机硫化合物阿霍烯可以通过诱导G 2 / M细胞周期停滞和凋亡来抑制肿瘤细胞的增殖。我们报告了一个简明的四步合成法的应用（Hunter等，2008 [1]），该合成法允许使用末端烯丙基被取代的阿霍恩类似物。经过测试的十二种此类衍生物的文库对WHCO1食道癌细胞的抗增殖活性，已鉴定出一种衍生物，该衍生物含有对-甲氧基苄基（PMB）取代的端基，其活性是Z-阿Z烯的十二倍，IC 50为50为2.1μM（Kaschula等，2011 [2]）。结构活性研究涉及该铅的亚砜和乙烯基二硫化物基团的修饰，发现该二硫化物是负责抑制WHCO1细胞生长，通过caspase-3激活诱导G 2 / M细胞周期停滞和凋亡的阿霍烯药效团，并且乙烯基基团将抗扩散活性进一步提高了八倍。铅与半胱氨酸在回流的THF中的反应作为基于硫醇/二硫键交换的阿霍内作用机理的模型反应的模型反应表明，二硫化乙烯基的烯丙基硫是交换中硫醇攻击的位点。
• 신규한 아조엔 유도체, 이의 제조방법 및 이를 유효 성분으로 함유하는 암의 예방 또는 치료용 약학적 조성물
  申请人：Sookmyung Women's university industry-academic cooperation foundation 숙명여자대학교산학협력단(220050092977) BRN ▼106-82-12227

  公开号：KR20180008350A

  公开（公告）日：2018-01-24

  본 발명은 신규한 아조엔 유도체, 이의 제조방법 및 이를 유효 성분으로 함유하는 암의 예방 또는 치료용 약학적 조성물에 관한 것으로, 본 발명에 따른 신규한 아조엔 유도체는 신장암 세포주(ACHN), 유방암 세포주(MDA-MB-231), 대장암 세포주(HCT-15), 전립선암 세포주(PC-3), 위암 세포주(NUGC-3), 및 폐암 세포주(NCI-H23)의 증식을 억제할 수 있는 것으로 확인되어, 이를 유효성분으로 함유하는 암의 예방 또는 치료용 약학적 조성물로 유용하게 사용될 수 있다.

  本发明涉及一种新的偶氮烯衍生物，其制备方法以及用作癌症预防或治疗药物组合物的有效成分，根据本发明，新的偶氮烯衍生物已被确认可以抑制肾癌细胞系(ACHN)，乳腺癌细胞系(MDA-MB-231)，结肠癌细胞系(HCT-15)，前列腺癌细胞系(PC-3)，胃癌细胞系(NUGC-3)和肺癌细胞系(NCI-H23)的增殖，因此可以作为用于癌症预防或治疗的药物组合物的有效成分。
• NOVEL ORGANIC SULFUR COMPOUND, METHOD FOR PREPARING SAME, AND PHARMACEUTICAL COMPOSITION FOR PREVENTING OR TREATING CANCER OR AN INFLAMMATORY DISEASE, CONTAINING SAME AS ACTIVE INGREDIENT
  申请人：SOOKMYUNG WOMENS UNIVERSITY INDUSTRY-ACADEMIC COOPERATION FOUNDATION

  公开号：US20210300865A1

  公开（公告）日：2021-09-30

  A novel organic sulfur compound, a method for preparing the same, and a pharmaceutical composition for preventing or treating cancer or inflammatory diseases, containing the same as an active ingredient are provided. The novel organic sulfur compound is capable of excellently inhibiting histone deacetylated (HDAC) enzymes in a concentration of nanomolar or micromolar units and has been found to have an excellent effect against inflammatory diseases, and has been found to be capable of inhibiting the proliferation of cancer.

  提供一种新型有机硫化合物，一种制备该化合物的方法，以及一种包含该化合物作为活性成分的用于预防或治疗癌症或炎症性疾病的药物组合物。这种新型有机硫化合物能够在纳摩尔或微摩尔单位的浓度下出色地抑制组蛋白去乙酰化酶（HDAC），已发现对炎症性疾病具有出色的作用，并且已发现能够抑制癌症的增殖。
• MUTILIN DERIVATIVE HAVING HETEROCYCLIC AROMATIC RING CARBOXYLIC ACID STRUCTURE IN SUBTITUENT AT 14-POSITION
  申请人：Fukuda Yasumichi

  公开号：US20100197909A1

  公开（公告）日：2010-08-05

  To provide a novel mutilin derivative having a substitution at the 14-position, which is a novel mutilin analogue exhibiting a potent and broad antimicrobial action against Gram-positive bacteria and Gram-negative bacteria including various drug-resistant bacteria, and which is expected to be useful as an agent for treating infectious diseases. A mutilin derivative represented by the following general formula (1): or a pharmaceutically acceptable addition salt thereof.

  提供一种在14位点具有取代基的新型多黏菌素衍生物，该新型多黏菌素类似物表现出强大而广泛的抗菌活性，可对抗革兰氏阳性菌和革兰氏阴性菌，包括各种耐药菌，并且预计可用作治疗传染病的药物。该多黏菌素衍生物由以下一般式（1）表示：或其药学上可接受的加盐物。