巯基甲基-琥珀酸 | 28525-49-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 巯基甲基-琥珀酸
• 英文名称: mercaptomethyl-succinic acid
• 英文别名: Mercaptomethyl-bernsteinsaeure；Thioitamalsaeure；mercaptomethylbutanedioic acid；2-(sulfanylmethyl)butanedioic acid
• CAS: 28525-49-7
• 化学式: C₅H₈O₄S
• 分子量: 164.182
• InChiKey: SVEXORXGIFDNOF-UHFFFAOYSA-N

物化性质

• 沸点：
  287.1±30.0 °C(Predicted)
• 密度：
  1.430±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  75.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  巯基甲基-琥珀酸 在 劳森试剂 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 24.5h， 生成 tetrahydro-5-thioxo-3-thiophenecarboxylic acid methyl ester
  参考文献：
  名称：

  A new type of plant activator: synthesis of thieno[2,3-d ][1,2,3]thiadiazole-6-carboxylic acid derivatives via Hurd–Mori cyclization

  摘要：

  我们提出了一种以廉价且容易获得的亚甲基丁二酸和硫代乙酸为起始原料的标题化合物的简短而有效的合成方法。优化的序列允许通过几个步骤大规模制备这种新型植物活化剂。邻位锂化用于将取代基引入5-位。建议对 Hurd–Mori 反应的反应机制进行修改来解释意外的芳构化。

  DOI：

  10.1039/a708375k
• 作为产物：
  描述：

  衣康酸 在 sodium hydroxide 、 水 作用下， 反应 19.0h， 生成 巯基甲基-琥珀酸
  参考文献：
  名称：

  A new type of plant activator: synthesis of thieno[2,3-d ][1,2,3]thiadiazole-6-carboxylic acid derivatives via Hurd–Mori cyclization

  摘要：

  我们提出了一种以廉价且容易获得的亚甲基丁二酸和硫代乙酸为起始原料的标题化合物的简短而有效的合成方法。优化的序列允许通过几个步骤大规模制备这种新型植物活化剂。邻位锂化用于将取代基引入5-位。建议对 Hurd–Mori 反应的反应机制进行修改来解释意外的芳构化。

  DOI：

  10.1039/a708375k

文献信息

• Microbicides
  申请人：Novartis Finance Corporation

  公开号：US05814629A1

  公开（公告）日：1998-09-29

  The invention relates to novel microbicidal and plant-immunising compounds of formula I ##STR1## wherein: X is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, SR.sub.8, N(R.sub.9)R.sub.10, CH.sub.2 OH, CHO or COOR.sub.8 ; R.sub.8 to R.sub.10 are hydrogen, C.sub.1 -C.sub.4 alkyl, benzyl, C.sub.1 -C.sub.4 acyl or benzoyl; Z is hydrogen, halogen, or a methyl group that is unsubstituted or to which from 1 to 3 unsubstituted or substituted hetero atoms O, S and/or N are bonded; in free form or in the form of salts. They can be used in crop protection for controlling and preventing disease infestation.

  本发明涉及一种新型杀菌和植物免疫化合物，其化学式为I ##STR1## 其中：X是氢、卤素、C.sub.1-C.sub.4烷基、SR.sub.8、N（R.sub.9）R.sub.10、CH.sub.2OH、CHO或COOR.sub.8；R.sub.8到R.sub.10是氢、C.sub.1-C.sub.4烷基、苯甲基、C.sub.1-C.sub.4酰基或苯甲酰基；Z是氢、卤素或一个未取代或与1到3个未取代或取代的杂原子O、S和/或N结合的甲基基团；以自由形式或盐的形式存在。它们可用于作物保护，控制和预防疾病侵染。
• Preparation of Carboxythiolactones and Their Active Derivatives
  作者：Bonnie J. Garbiras、Stephen Marburg

  DOI：10.1055/s-1999-3377

  日期：1999.2

  The design of peptidyl immunogens requires that a number of elements be covalently linked to enable the appropriate immune response to occur. Two of these elements are: (a) T-cell sequences which after processing, bind to major histocompatibility complex (MHC) molecules and T-cell receptors and (b) B-cell sequences which embody the constellation of atoms which will ultimately be recognized by the desired antibody. Our concept, designed to effectuate this, involved a single molecule which could conjugate three peptides, potentially in discrete steps, in one pot. Activated carboxythiolactones, hitherto unknown entities, provide such a system: two acyl sites susceptibile to nucleophilic attack at disparate rates and a liberated thiol susceptible to electrophilic alkylation. Such a set of thiolactones and their derivatives have been synthesized from inexpensive starting materials and their reactivities are under investigation. If successful, the system will not only obviate the difficult syntheses of longer linear peptides, but will also allow a rapid structural permutation of the various elements.

  肽基免疫原的设计需要将许多元件共价连接以能够发生适当的免疫反应。其中两个元素是：(a) T 细胞序列，经过加工后，与主要组织相容性复合体 (MHC) 分子和 T 细胞受体结合；(b) B 细胞序列，包含最终将被识别的原子群通过所需的抗体。我们的概念旨在实现这一目标，涉及单个分子，该分子可以在一锅中以不连续的步骤结合三个肽。迄今为止未知的活化的羧基硫内酯提供了这样的系统：两个对不同速率的亲核攻击敏感的酰基位点和一个对亲电烷基化敏感的释放的硫醇。这样一组硫内酯及其衍生物已经由廉价的起始原料合成，并且它们的反应性正在研究中。如果成功，该系统不仅将消除较长线性肽的困难合成，而且还将允许各种元素的快速结构排列。
• Adrenal Insufficiency in Critically Ill Emergency Department Patients: A Taiwan Preliminary Study
  作者：Shy-Shin Chang、Shiumn-Jen Liaw、Michael J. Bullard、Te-Fa Chiu、Jih-Chang Chen、How-Chin Liao

  DOI：10.1111/j.1553-2712.2001.tb00202.x

  日期：2001.7

  Objective: Unrecognized adrenal insufficiency can have serious consequences in critically ill emergency department (ED) patients. This prospective pilot study of adrenal function in patients with severe illness was undertaken to determine the prevalence of adrenal dysfunction and any relation to prior herbal drug use. Methods: In a high‐volume urban tertiary care ED, adult patients with sepsis or acute myocardial infarction (AMI) were eligible for the study. Over a two‐month period, a convenience sample was enrolled by the authors on arrival to the ED. Inclusion criteria were systemic inflammatory response syndrome (SIRS) criteria plus evidence of at least one organ dysfunction or cardiac marker plus electrocardiogram‐proven AMI. Exclusion criteria included known corticosteroid use. Serum cortisol was measured on arrival and for those patients with a level of <15 μg/dL (<414 nmol/L), an adrenocorticotropic hormone (ACTH) stimulation test was performed. Results: Of the 30 enrolled patients, 23 (77%) were suffering from severe sepsis and the other seven (23%) had an AMI. Thirteen of the 30 patients (43%; 95% CI = 25% to 65%) had serum cortisol levels of <15 μg/dL, consistent with adrenal insufficiency, nine with severe sepsis and four with an AMI. Eight (62%; 95% CI = 32% to 86%) of the 13 patients with low cortisol levels reported using herbal medications, while only two (12%; 95% CI = 1% to 36%) of the 17 with normal cortisol levels reported taking herb drugs (p = 0.01). Only two (15%; 95% CI = 2% to 45%) of the patients with low cortisol levels failed their corticotropin stimulation test, suggestive of true adrenocortical insufficiency. Both reported using herbal preparations. Conclusions: These results indicate that adrenal dysfunction is common among a group of critically ill patients seen in this Taiwanese ED. Moreover, the use of herbal drugs was high in the patients with low serum cortisols. Further studies are required to both confirm these findings and clarify whether a number of herbal medications contain corticosteroids.

  目标: 未被识别的肾上腺功能不全在危重急诊室（ED）患者中可能会导致严重后果。本文前瞻性试点研究严重疾病的患者的肾上腺功能，旨在确定肾上腺功能障碍的发病率及其与先前草药药物使用之间的任何关联。方法: 在一家高容量的城市三级护理急诊科，符合研究条件的患者是患有败血症或急性心肌梗死（AMI）的成年患者。在两个月期间，符合条件的患者在抵达急诊科时由研究者们 recruiting。纳入标准是全身性炎症反应综合征（SIRS）标准加上至少一个器官功能障碍或心脏标志物阳性，且心电图证实为AMI。排除标准包括已知的类固醇药物使用。在患者抵达时测量血清皮质醇水平，对于血清皮质醇水平小于15 μg/dL（小于414 nmol/L）的患者，进行了促肾上腺皮质激素（ACTH）刺激试验。结果: 在招募的30名患者中，23名（77%）患有严重败血症，另外7名（23%）患有AMI。30名患者中，13名（43%；95% CI = 25%至65%）的血清皮质醇水平小于15 μg/dL，与肾上腺功能不全一致，其中9名患有严重败血症，4名患有AMI。13名低皮质醇水平患者中，有8名（62%；95% CI = 32%至86%）报告使用过草药药物，而17名正常皮质醇水平患者中，只有2名（12%；95% CI = 1%至36%）报告使用过草药药物（p = 0.01）。在13名低皮质醇患者中，只有2名（15%；95% CI = 2%至45%）的促肾上腺皮质激素刺激试验失败，提示真正的肾上腺皮质功能不全。这2名患者都报告使用过草药制剂。结论: 这些结果显示，在本研究中的台湾急诊室患者中，肾上腺功能障碍在危重病患者中很常见。此外，低血清皮质醇患者的草药药物使用率较高。需要进一步的研究来证实这些发现，并阐明多种草药药物是否含有类固醇。
• Schjanberg, Chemische Berichte, 1942, vol. 75, p. 468,479 - 481
  作者：Schjanberg

  DOI：——

  日期：——
• A new type of plant activator: thieno[2,3-<i>d</i>][1,2,3]thiadiazole-6-carboxylic acid derivatives
  作者：Peter Stanetty、Manfred Kremslehner、Marion Jaksits

  DOI：10.1002/(sici)1096-9063(1998110)54:3<316::aid-ps838>3.0.co;2-c

  日期：1998.11

  A short and efficient synthesis of a series of the title compounds is presented starting with methylenebutanedioic acid and thioacetic acid. Using the: Hurd-Mori reaction in the key step, the optimised reaction sequence allows the large-scale preparation of this new type of plant activator in a few steps with a high overall yield. Additional functionalisation of the 5-position via directed ortho-lithiation methodology is also described. (C) 1998 Society of Chemical Industry.