S-allylmercapto-L-cysteine | 2281-22-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: S-allylmercapto-L-cysteine
• 英文别名: (S)-allylmercaptocysteine；SAMC；(2R)-2-azaniumyl-3-(prop-2-enyldisulfanyl)propanoate
• CAS: 2281-22-3
• 化学式: C₆H₁₁NO₂S₂
• 分子量: 193.291
• InChiKey: WYQZZUUUOXNSCS-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  S-allylmercapto-L-cysteine 在 高氯酸 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 1.67h， 生成 (2R)-2-(2-(acetoxy)-3-(3,4-bis(acetoxy)phenyl)propionylamino)3-(allyldithio)-propionic acid
  参考文献：
  名称：

  丹参素与H2S/NO供体结合物及其制备方法和在制药中的应用

  摘要：

  本发明属化学制药领域，涉及中草药丹参中有效成分丹参素与H 2 S/NO供体的结合物及其制备方法和在制药中的应用，尤其是在制备防治心脑血管和炎症相关疾病药物中的用途。本发明通过体外氧化应激损伤和炎症模型实验，结果显示所述的结合物能显著抑制H 2 O 2 诱导的SH‑SY5Y细胞氧化应激损伤，对损伤细胞具有明显的保护作用；能显著抑制内毒素(LPS)诱导的小鼠腹腔巨噬细胞分泌炎性介质，减少炎症诱导的一氧化氮和炎性细胞因子的释放；体内活性实验结果显示，所述的结合物对LPS诱导的小鼠腹膜炎能改善小鼠的凝血时间，明显抑制小鼠腹腔的炎性细胞因子的释放，结果表明所述化合物可用于制备防治心脑血管疾病和炎症性疾病的药物。

  公开号：

  CN111484413A
• 作为产物：
  描述：

  大蒜素 在 endogenous γ-glutamyl transpeptidase 、 水 作用下， 以 水 为溶剂， 反应 73.0h， 生成 S-allylmercapto-L-cysteine
  参考文献：
  名称：

  Changes of S-Allylmercaptocysteine and γ-Glutamyl-S-allylmercaptocysteine Contents and Their Putative Production Mechanisms in Garlic Extract during the Aging Process

  摘要：

  gamma-Glutamyl-S-allylmercaptocysteine (GSAMC), a putative precursor compound of S-allylmercaptocysteine (SAMC), was isolated and identified from aged garlic extract (AGE). We analyzed the change of their contents in AGE during the aging process, chronologically from 1 to 22 months. The formation of these compounds occurred mostly during the early stage of the aging period: the SAMC content reached a maximum at approximately 4 months, whereas the GSAMC content reached a maximum at 1 month and then decreased during the subsequent aging period. To assess the possible relationship between the change of the two compounds during the aging process, we set up the model reactions with the hypothesis that GSAMC is produced from gamma-glutamyl-S-allylcysteine (GSAC)/gamma-gultamyl-S-1-propenylcysteine (GS1PC) and that SAMC is produced from GSAMC by endogenous gamma-glutamyl transpeptidase (GGT) in garlic during the early stage of the aging process. We found that, in the model reactions, SAMC was produced from GSAMC by the garlic protein fraction having GGT activity and its production was suppressed by a GGT inhibitor. Furthermore, the production of GSAMC from allicin and GSAC/GS1PC was found in another model reaction. The reaction between allicin and GS1PC was faster than that between allicin and GSAC and, thus, may be involved in the production of GSAMC in the early stage of the aging process.

  DOI：

  10.1021/acs.jafc.8b02541

文献信息

• Sulfur containing compounds
  申请人：——

  公开号：US20030220524A1

  公开（公告）日：2003-11-27

  This invention is directed to novel and known stufur containing compounds and pharmaceutically acceptable salts thereof that have utility as antifungals and as antiproliferative agents against mammalian cells, in particular cancer cells and most particularly leukemia-derived cells. The invention provides a method for synthesizing certain of the sulfur containing compounds that is more efficient than previously known methods.

  这项发明涉及新颖且已知的含有硫的化合物以及具有抗真菌活性和作为哺乳动物细胞，特别是癌细胞，尤其是白血病来源细胞的抗增殖剂的药用可接受盐。发明提供了一种合成某些含硫化合物的方法，该方法比先前已知的方法更有效。
• 1H-pyrrole-2,4-dicarbonyl-derivatives and their use as flavoring agents
  申请人：IMAX Discovery GmbH

  公开号：EP2832233A1

  公开（公告）日：2015-02-04

  The present invention primarily relates to 1H-pyrrole-2,4-dicarbonyl-derivatives of Formula (I) wherein R1, R2, R3, Z. Z' and J are as defined in the description, to mixtures thereof and to the use thereof as flavoring agents. The compounds in accordance with the present invention are suitable for producing, imparting, or intensifying an umami flavor. The invention further relates to flavoring mixtures, compositions for oral consumption as well as ready-to-eat, ready-to-use and semifinished products, comprising an effective amount of the compound of Formula (I) or of a mixture of compounds of Formula (I) and to specific methods for producing, imparting, modifying and/or intensifying specific flavor impressions.

  本发明主要涉及式(I)的1H-吡咯-2,4-二羰基衍生物，其中R1、R2、R3、Z、Z'和J按描述定义，及其混合物，以及用作调味剂的使用。根据本发明的化合物适用于生产、赋予或增强鲜味。本发明进一步涉及包含式(I)化合物或式(I)化合物混合物的有效量的调味混合物、口腔消费的组成物以及即食、即用和半成品，以及用于生产、赋予、改变和/或增强特定风味印象的特定方法。
• Imidazo[1,2-a]pyridine-ylmethyl-derivatives and their use as flavoring agents
  申请人：IMAX Discovery GmbH

  公开号：EP2832234A1

  公开（公告）日：2015-02-04

  The present invention primarily relates to imidazo[1,2-a]pyridine-ylmethyl-derivatives of Formula (I) wherein R1, R2, X, W e J are as defined in the description, to mixtures thereof and to the use thereof as flavoring agents. The compounds in accordance with the present invention are suitable for producing, imparting, or intensifying an umami flavor. The invention further relates to flavoring mixtures, compositions for oral consumption as well as ready-to-eat, ready-to-use and semifinished products, comprising an effective amount of the compound of Formula (I) and to specific methods for producing, imparting, modifying and/or intensifying specific flavor impressions.

  本发明主要涉及式(I)的咪唑[1,2-a]吡啶基甲基衍生物，其中R1、R2、X、W和J如描述中定义，以及涉及它们的混合物和使用它们作为调味剂。根据本发明的化合物适合于产生、赋予或增强鲜味。本发明进一步涉及调味混合物、口腔摄入的配方以及包含有效量的式(I)化合物的即食、即用和半成品，以及用于生产、赋予、改变和/或增强特定风味印象的特定方法。
• Antibacterial Potential of Garlic-Derived Allicin and Its Cancellation by Sulfhydryl Compounds
  作者：Hiroyuki FUJISAWA、Kazuhiro WATANABE、Kaoru SUMA、Kana ORIGUCHI、Hiroshi MATSUFUJI、Taiichiro SEKI、Toyohiko ARIGA

  DOI：10.1271/bbb.90096

  日期：2009.9.23

  Allicin (allyl 2-propenethiosulfinate), an antibacterial principle of garlic, has drawn much attention, since it has potent antimicrobial activity against a range of microorganisms, including methicillin-resistant Staphylococcus aureus. There have been many reports on the antibacterial properties of allicin, but no quantitative comparison of antibacterial activities between freshly prepared garlic extract and clinically useful antibiotics has been performed. To verify the substantial antibacterial effect of aqueous garlic extract, we compared it with those of allicin and several clinically useful antibiotics using two representative bacteria commonly found in the human environment, Gram-positive S. aureus and Gram-negative Escherichia coli. The garlic extract had more potent anti-staphylococcal activity than an equal amount of allicin. In terms of antibiotic potency against Gram-positive and Gram-negative bacteria, authentic allicin had roughly 1–2% of the potency of streptomycin (vs.  S. aureus), 8% of that of vancomycin (vs.  S. aureus), and only 0.2% of that of colistin (vs.  E. coli). The antibacterial activity of allicin was completely abolished by cysteine, glutathione and coenzyme A, but not by non-SH-compounds. The oxygen in the structure (–S(=O)–S–) of allicin therefore functions to liberate the S-allyl moiety, which might be an offensive tool against bacteria.

  大蒜素（2-丙烯基硫代亚磺酸酯）是大蒜中的一种抗菌成分，因其对包括耐甲氧西林金黄色葡萄球菌在内的一众微生物具有强效的抗微生物活性而引起了广泛关注。虽然已有许多报道介绍了大蒜素的抗菌特性，但还没有实验进行过新制备的大蒜提取液和临床用抗生素之间抗菌活性的定量比较。为了证实水溶性大蒜提取液具有显著的抗菌效果，我们将其抗菌活性与大蒜素及数种临床可用抗生素进行了比较，采用的实验菌株为两种在人体环境中常见的细菌，即革兰氏阳性菌金黄色葡萄球菌和革兰氏阴性菌大肠杆菌。大蒜提取液对金黄色葡萄球菌的抗菌活性较相同量的大蒜素更强。就抗生素对革兰氏阳性和革兰氏阴性菌的抗菌效力而言，纯大蒜素大致具有链霉素（对金黄色葡萄球菌）1~2%的效力，万古霉素（对金黄色葡萄球菌）8%的效力，以及多粘菌素（对大肠杆菌）0.2%的效力。半胱氨酸、谷胱甘肽和辅酶A能够完全消除大蒜素的抗菌活性，而非巯基化合物则不能。因此大蒜素结构（-S(=O)-S-）中的氧具有释放S-丙烯基的作用，这可能是大蒜素对抗细菌的一种手段。
• USE OF ALLYLCYSTEINE OR ITS ANALOGS AND PHARMACEUTICAL COMPOSITION THREROF
  申请人：Fudan University

  公开号：EP2186512A1

  公开（公告）日：2010-05-19

  The invention discloses a use of compound S-allyl cysteine or its analogues in preparation of medicaments for preventing or treating myocardial injury and a preparation method thereof, as well as a pharmaceutical composition comprising the compound.

  该发明揭示了利用复合S-烯丙基半胱氨酸或其类似物制备用于预防或治疗心肌损伤的药物以及其制备方法，以及包含该化合物的药物组合物。