3-(acetylthio)benzoic acid | 90887-44-8

• 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: 3-(acetylthio)benzoic acid
• 英文别名: 3-acetylsulfanylbenzoic acid
• CAS: 90887-44-8
• 化学式: C₉H₈O₃S
• 分子量: 196.227
• InChiKey: CKBDDIOFRDYYFZ-UHFFFAOYSA-N

物化性质

• 熔点：
  152-153 °C(Solv: benzene (71-43-2); hexane (110-54-3))
• 沸点：
  370.5±25.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)
• 保留指数：
  1738

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  79.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(acetylthio)benzoic acid 在 sodium hydroxide 、 三甲基氯硅烷 、 N,N'-二环己基碳二亚胺 、 sodium iodide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.5h， 生成 [Cyclopentyl-(3-mercapto-benzoyl)-amino]-acetic acid
  参考文献：
  名称：

  Angiotensin converting enzyme inhibitors. (Mercaptoaroyl)amino acids

  摘要：

  A series of (mercaptoaroyl)amino acids and related compounds was synthesized and tested for ability to inhibit angiotensin converting enzyme (ACE). The most active compound was N-(3-chloro-2-mercaptobenzoyl)-N-cyclopentylglycine, having an in vitro I50 = 0.28 microM. Substitution of the aromatic 3-position by small polar groups enhanced ACE inhibitory activity, whereas bulky groups diminished it. Alteration of the beta relationship between the mercaptan and amide carbonyl or masking of the thiol by acylation reduced activity. Replacement of the thiol by nitro, hydroxy, or carboxy gave compounds lacking ACE inhibitory activity.

  DOI：

  10.1021/jm00381a012
• 作为产物：
  描述：

  3-巯基苯甲酸 、 乙酸酐 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 1.0h， 以88%的产率得到3-(acetylthio)benzoic acid
  参考文献：
  名称：

  コンホメーションを固定された、合成マクロ環化合物

  摘要：

  胃肠道运动减慢障碍，如糖尿病性胃轻瘫和便秘型过敏性肠症候群；中枢神经系统相关疾病，如偏头痛、精神分裂症、精神病或抑郁症；以及治疗青光眼和早产相关眼高压症的有效化合物的提供。通过代表为方案6实施例1中所示的化合物，具有固定构象，对莫钦受体（MR受体）、5-羟色胺受体的5-HT2B亚型（5-HT2B受体）和前列腺素F2α受体（FP受体）具有激动剂或拮抗剂活性的12-30环大环化合物。【选择图】无

  公开号：

  JP2017160247A

文献信息

• [EN] CONFORMATIONALLY CONSTRAINED, FULLY SYNTHETIC MACROCYCLIC COMPOUNDS<br/>[FR] COMPOSÉS MACROCYCLIQUES ENTIÈREMENT SYNTHÉTIQUES, À CONFORMATION CONTRAINTE
  申请人：POLYPHOR AG

  公开号：WO2011015241A1

  公开（公告）日：2011-02-10

  Conformationally restricted, spatially defined 12-30 membered macrocyclic ring systems of type (I) are constituted by three distinct building blocks: an aromatic template a, a conformation modulator b and a spacer moiety c as detailed in the description and the claims. Macrocycles of type (I) are readily manufactured by parallel synthesis or combinatorial chemistry. They are designed to interact with specific biological targets. In particular, they show agonistic or antagonistic activity on the motilin receptor (MR receptor), on the serotonin receptor of subtype 5-HT2B (5-HT2B receptor), and on the prostaglandin F2 • receptor (FP receptor). They are thus potentially useful for the treatment of hypomotility disorders of the gastrointestinal tract such as diabetic gastroparesis and constipation type irritable bowl syndrome; of CNS related diseases like migraine, schizophrenia, psychosis or depression; of ocular hypertension such as associated with glaucoma and preterm labour.

  构象受限、空间定义的12-30元大环环系统(I型)由三个不同的构建模块组成：芳香模板a、构象调节剂b和间隔基团c，详细描述在说明书和专利要求中。I型大环可通过并行合成或组合化学方法轻松制备。它们设计用于与特定生物靶点相互作用。特别是，它们在胃动素受体(MR受体)、5-羟色胺受体亚型5-HT2B(5-HT2B受体)和前列腺素F2•受体(FP受体)上显示激动或拮抗活性。因此，它们潜在用于治疗胃肠道低动力障碍，如糖尿病性胃轻瘫和便秘型肠易激综合征；中枢神经系统相关疾病，如偏头痛、精神分裂症、精神病或抑郁症；眼压增高，如青光眼和早产。
• CONFORMATIONALLY CONSTRAINED, FULLY SYNTHETIC MACROCYCLIC COMPOUNDS
  申请人：Obrecht Daniel

  公开号：US20120270881A1

  公开（公告）日：2012-10-25

  Conformationally restricted, spatially defined 12-30 membered macrocyclic ring systems of formulae Ia and Ib are constituted by three distinct molecular parts: Template A, conformation Modulator B and Bridge C. These macrocycles Ia and Ib are readily manufactured by parallel synthesis or combinatorial chemistry in solution or on solid phase. They are designed to interact with a variety of specific biological target classes, examples being the agonistic or antagonistic activity on G-protein coupled receptors (GPCRs), ion channels and signal transduction pathways. In particular, these macrocycles act as antagonists of the motilin receptor, the FP receptor and the purinergic receptors P2Y 1 , as modulators of the serotonin receptor of subtype 5-HT 2B , as blockers of the voltage-gated potassium channel K v 1.3 and as inhibitors of the β-catenin-dependent “canonical” Wnt pathway. Thus they are showing great potential as medicaments for a variety of diseases.

  具有结构限制的、空间定义的12-30环的大环系统Ia和Ib由三个不同的分子部分构成：模板A、构象调节剂B和桥C。这些大环Ia和Ib可以通过并行合成或溶液中或固相上的组合化学来轻松制备。它们被设计用于与各种特定的生物靶标类相互作用，例如对G蛋白偶联受体（GPCRs）、离子通道和信号转导途径的激动或拮抗活性。特别地，这些大环作为莫蒂林受体的拮抗剂、FP受体和嘌呤受体P2Y1的调节剂、5-HT2B亚型的5-羟色胺受体的调节剂、电压门控钾通道Kv1.3的阻断剂以及β-连环蛋白依赖的“经典”Wnt途径的抑制剂。因此，它们显示出作为各种疾病药物的巨大潜力。
• 构象受限的完全合成的大环化合物
  申请人：波利弗尔股份公司

  公开号：CN105294732B

  公开（公告）日：2018-09-25

  类型(I)的构象受限的、空间限定的12‑30元大环环系包括三个不同的构造单元：芳族模板a，构象调节物b和间隔体部分c，如说明书和权利要求所详细描述。类型(I)大环通过平行合成或组合化学容易地制备。它们设计用来与特定的生物学靶标相互作用。尤其是，它们显示对下述的激动或拮抗活性：胃动素受体(MR受体)，亚型5‑HT2B的5‑羟色胺受体(5‑HT2B受体)，和前列腺素F2α受体(FP受体)。从而，它们有效地用于治疗胃肠道运动减弱障碍比如糖尿病性胃轻瘫和便秘型肠易激综合征；与CNS有关的疾病比如偏头痛，精神分裂症，精神病或抑郁；高眼压症比如与青光眼有关的高眼压症和早产。
• PROCESS FOR PRODUCING POLYMER TERMINATED WITH OPTIONALLY PROTECTED FUNCTIONAL GROUP
  申请人：KURARAY Co. LTD.

  公开号：EP0704460A1

  公开（公告）日：1996-04-03

  A process for producing polymers having terminal functional group which may be protected, comprises polymerizing a radical-polymerizable monomer with a polymerization initiator comprising at least one member selected from the group (A) consisting of thio-S-carboxylic acids represented by the following general formula (1) and dithiocarboxylic acids represented by the following general formula (2) and at least one member selected from the group (B) consisting of polysulfides represented by the following general formula (3), polysulfides represented by the following general formula (4) and sulfoxides: wherein R¹ represents a hydrocarbon group which may have a substituent including functional group; wherein R² represents a hydrocarbon group which may have a substituent including functional group; wherein R³ and R⁴ each represents a hydrocarbon group which may have a substituent including functional group and n is an integer of 2 or more; and         R⁵- (S)m- R⁶     (4) wherein R⁵ and R⁶ each represents a hydrocarbon group having a functional group and m is an integer of 2 or more. This process can produce polymers with which functional groups have been introduced into one end or both ends thereof, irrespective of the rate of polymerization or the degree of polymerization of the polymer that forms.

  一种生产具有可被保护的末端官能团的聚合物的工艺，包括用聚合引发剂聚合可自由基聚合的单体，聚合引发剂包括至少一种选自以下通式(1)代表的硫代-S-羧酸和以下通式(2)代表的二硫代羧酸组成的基团(A)，以及至少一种选自以下通式(3)代表的多硫化物、以下通式(4)代表的多硫化物和氧化硫组成的基团(B)： 其中 R¹ 代表烃基，该烃基可能具有包括官能团在内的取代基； 其中 R² 代表可具有包括官能团在内的取代基的烃基； 其中 R³ 和 R⁴ 各自代表一个可具有包括官能团在内的取代基的烃基，且 n 为 2 或 2 以上的整数；以及 R⁵- (S)m- R⁶ (4) 其中，R⁵ 和 R⁶ 分别代表具有官能团的烃基，m 为 2 或 2 以上的整数。无论聚合速度或形成的聚合物的聚合度如何，该工艺都能生产出在一端或两端引入官能团的聚合物。
• Conjugative Effects in Divalent Sulfur Groupings¹
  作者：F. G. Bordwell、Pierre J. Boutan

  DOI：10.1021/ja01585a041

  日期：1956.2